Diethyl Ether → Methyl 2-Amino-4-bromobenzoate

HRID 2173223Notes

Reaction equation

HRID 2173223 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:12]COCC>>[NH2:1][C:2]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:12])=[O:5]

Participants

3

Reactant 2

HCID 3283Diethyl EtherHCID 886912-Amino-4-bromobenzoic acid

Product 1

HCID 17871390Methyl 2-Amino-4-bromobenzoate

Procedure

A solution of 2-amino-4-bromobenzoic acid (500 mg, 2.3 mmol) in 20 mL of Et2O was cooled to 0° C. by ice water, and a solution of CH2N2 (145 mg, 3.5 mmol) was added. The reaction was warmed to r.t and stirred for 12 hours. The reaction mixture was concentrated to give methyl 2-amino-4-bromobenzoate 1H-NMR (400 MHz, CDCl3) δ 11.45 (s, 1H), 7.95-8.05 (in, 2H), 7.72 (d, J=8.0 Hz, 1H), 3.31 (s, 3H).

Workup

  1. temperatureThe reaction was warmed
  2. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-ab9cb86f68db429a997359edadcd04c5
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

Loading…