4-(2-Bromoethyl)benzoic acid → Methyl 4-(2-bromoethyl)benzoate

HRID 2218213Notes

Reaction equation

HRID 2218213 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[Br:8][CH2:9][CH2:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1>CCCCCC.C(Cl)Cl.CO>[Br:8][CH2:9][CH2:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([O:17][CH3:1])=[O:16])=[CH:13][CH:12]=1

Participants

6

Reactant 2

HCID 1040684-(2-Bromoethyl)benzoic acidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 10586287Methyl 4-(2-bromoethyl)benzoateYield 100%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

A 2 M solution in hexane of trimethylsilyldiazomethane (0.072 mol, 36 mL) was added dropwise to a solution of 4-(bromoethyl)benzoic acid (15 g, 0.065 mol) in DCM (150 mL) and MeOH (36 mL). The resulting solution was stirred at RT for 2 h then was concentrated under reduced pressure to afford the title compound (15.8 g, 98%) as a pale yellow oil. 1H NMR (CDCl3) δ 3.2 (t, 2H), 3.6 (t, 2H), 3.9 (s, 3H), 7.3 (d, 2H), 8.0 (d, 2H).

Workup

  1. concentrationthen was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c8ef42a61e714b239b3253d0727a6755
Source dataset
uspto-grants-2008_08
Patent number
US07410991B2

Reaction notes

Loading…