2-Bromoanisole → 2,2'-Dimethoxybiphenyl

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1Br.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1B(O)O>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[O:11][CH3:10]

Participants

Reactant 2

HCID 113582-Bromoanisole

HCID 27339582-Methoxyphenylboronic acid

Product 1

HCID 6118162,2'-DimethoxybiphenylYield 71%

Procedure

From 2-methoxy-bromobenzene and 2-methoxyphenyl boronic acid, yield 71%; mp 155-157° C. (lit.,4 155° C.); IR: 1590, 1501, 1481, 1455 and 1238; 1H NMR (400 MHz; CDCl3): 7.34 (2H, m), 7.25 (2H, d, J 8), 7.02-6.97 (4H, m) and 3.77 (6H, s); 13C NMR (CDCl3): 157, 131.4, 128.5, 127.8, 120.3, 111.1 and 55.6; m/z (EI) 214 (100%, M+), 184 (50) and 69 (40)(Found: M+, 214.099. C12H14O2 requires M, 214.099).

Workup

custommp 155-157° C. (lit.,4 155° C.)

Sources & evidence

ORD record: ord-7674ec50e34b43d0a57f7e2556082012
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08828902B2

Reaction notes

Loading…