Electric Literature of 698-00-0, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 698-00-0, name is 2-Bromo-N,N-dimethylaniline, This compound has unique chemical properties. The synthetic route is as follows.
Synthesis of 2-(di-l-adamantylphosphino)-N^V-dimethylaniline (L2).[0287] Pd(OAc)2 (6.3 mg, 0.028 mmol) was added to a glass vial and dissolved in toluene (2 mL). This solution was then transferred to a vial containing DiPPF(l,l’-bis(diisopropylphosphino)ferrocene; 14.2 mg, 0.034 mmol) and was left to stir for 10 minutes. To a separate glass vial containing NaOtBu (192 mg, 2.0 mmol) was added a solution of (l-adamantyl)2PH (410 mg, 1.36 mmol) in 2 mL toluene, followed by2-bromo-NjV-dimethylaniline (230 L, 1.4 mmol), and the Pd(OAc)2/DiPPF solution, after which the vial was sealed with a cap containing a PTFE septum. The mixture was stirred for 20 h at 110 C, at which point the reaction was deemed complete on the basis of 31P NMR data obtained from an aliquot of the reaction mixture. The reaction mixture was then allowed to cool and was passed through a plug of silica, followed by washing of the plug with 40 mL of CH2C12. The combined eluent was collected and the solvent was removed in vacuo. The resulting pale orange solid was washed with cold hexanes (2 x 4 mL). Removal of volatile materials in vacuo yielded the product as an off-white powder (0.424 g, 1.01 mmol; 74 % yield). 1H NMR (CDC13): delta 7.71 (m, 1H, Ar-H), 7.32 (m, 1H, Ar-H), 7.20 (m, 1H, Ar-H), 7.05 (m, 1H, Ar-H), 2.71 (s, 6H, N(CH3)2), 2.01-1.89 (m, 18Eta, 1-Ad), 1.67 (s, 12Eta, 1-Ad). 13C{ ‘H} NMR (CDCI3): delta 161.6 (d, JPC = 21.6 Hz, Cquat), 137.4 (d, JPC = 3.3 Hz), 131.1 (d, JPC = 22.9 Hz, Cquat), 129.6, 122.2, 120.6 (d, Jpc = 3.9 Hz), 46.1 (d, Jpc = 4.2 Hz, N(CH3)2), 41.8 (d, Jpc = 13.0 Hz, CH2), 37.1 (CH2), 29.0 (d, /PC = 8.6 Hz, CH). 31P{ 1H} NMR (CDC13): delta 20.1. HRMS (ESI/[M+H]+) calcd. for C28H40N1P1: 422.2971. Found: 422.2978. Anal. Calcd for C^fttoPiNi: C 79.77; H 9.56; N 3.32. Found: C 79.47; H 9.46; N 3.31.
The chemical industry reduces the impact on the environment during synthesis 2-Bromo-N,N-dimethylaniline. I believe this compound will play a more active role in future production and life.
Reference:
Patent; DALHOUSIE UNIVERSITY; LUNDGREN, Rylan, J.; STRADIOTTO, Mark; WO2012/68335; (2012); A2;,
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