Dimethylamine → 1-(4-bromo-2,6-difluorophenyl)-N,N-dimethylmethanamine

Reaction equation

[Br:1][C:2]1[CH:9]=[C:8]([F:10])[C:5]([CH:6]=O)=[C:4]([F:11])[CH:3]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:26][NH:27][CH3:28]>>[Br:1][C:2]1[CH:9]=[C:8]([F:10])[C:5]([CH2:6][N:27]([CH3:28])[CH3:26])=[C:4]([F:11])[CH:3]=1

Participants

Reactant 3

HCID 674Dimethylamine

HCID 27732904-Bromo-2,6-difluorobenzaldehyde

HCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 667304921-(4-bromo-2,6-difluorophenyl)-N,N-dimethylmethanamineYield 80%

Procedure

According to procedure for the synthesis of Example A211A, by using 4-bromo-2,6-difluorobenzaldehyde (500 mg, 2.26 mmol), sodium triacetoxyborohydride (959 mg, 4.52 mmol) and 2M dimethylamine solution (2.626 mL, 4.52 mmol) to give the title compound as a colorless oil (452 mg, 79%). 1H NMR (400 MHz, CDCl3) δ 7.09 (d, J=6.8 Hz, 2H), 3.54 (s, 2H), 2.26 (s, 6H); MS ESI 249.9 [M+H]+, calcd for [C9H10BrF2N+H]+ 249.0.

Sources & evidence

ORD record: ord-af1d6268754d4fb3b647b6320d2ac259
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999968B2

Reaction notes

Loading…