Triethylamine → Methyl 3-(2-bromoacetamido)benzoate

HRID 600927Notes

Reaction equation

HRID 600927 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(N(CC)CC)C.[Br:19][CH2:20][C:21](Br)=[O:22]>ClCCl>[CH3:8][O:7][C:5](=[O:6])[C:4]1[CH:9]=[CH:10][CH:11]=[C:2]([NH:1][C:21](=[O:22])[CH2:20][Br:19])[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 78274Benzoic acid, 3-amino-, methyl ester

Product 1

HCID 20317589Methyl 3-(2-bromoacetamido)benzoateYield 99.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 3-aminobenzoate (4.53 g, 30.0 mmol) and triethylamine (3.54 g, 4.88 mL, 35.0 mmol) in dichloromethane (100 mL), at 0° C. while stirring, was added bromoacetyl bromide (6.66 g, 2.9 mL, 33.0 mmol) dropwise. After the addition, the mixture was stirred at room temperature overnight and passed through a short silica pad. The crude product, 3-(2-bromoacetylamino)benzoic acid methyl ester (8.09 g, 99.1%), obtained after the removal of the solvent (>99% by LC/MS, MS (ES+) m/z: 272, 274) was used without further purification.

Workup

  1. additionAfter the addition

Sources & evidence

ORD record
ord-8e2d00752db54daa8c42308f9c744777
Source dataset
uspto-grants-2011_03
Patent number
US07902241B2

Reaction notes

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