Azobisisobutyronitrile → 4-{2-[(3-Bromomethylbenzofuran-2-carbonyl)amino]ethoxy}benzoic acid methyl ester

HRID 2111147Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][NH:13][C:14]([C:16]2[O:17][C:18]3[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=3[C:20]=2[CH3:21])=[O:15])=[CH:6][CH:5]=1.N(C(C)(C)C#N)=NC(C)(C)C#N.[Br:39]N1C(=O)CCC1=O>ClC1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:5]=[CH:6][C:7]([O:10][CH2:11][CH2:12][NH:13][C:14]([C:16]2[O:17][C:18]3[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=3[C:20]=2[CH2:21][Br:39])=[O:15])=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 4-{2-[(3-methylbenzofuran-2-carbonyl)amino]ethoxy}benzoic acid methyl ester (0.340 mol) in chlorobenzene (1000 ml) was treated with 2,2′-azobisisobutyronitrile (5.60 g, 0.017 mol) and N-bromosuccinimide (75.76 g, 0.426 mol). The resulting mixture is heated to 80° C. and stirred for one hour. After completion of reaction, the reaction mixture was cooled to ambient temperature and washed with water, 3% sodium hydrogensulfite, and again with water. Solvent was distilled under reduced pressure and after cooling to ambient temperature, dichloromethane was added and to give 4-{2-[(3-bromomethylbenzofuran-2-carbonyl)amino]ethoxy}benzoic acid methyl ester which was used in the next step.

Workup

customAfter completion of reaction
temperaturethe reaction mixture was cooled to ambient temperature
washwashed with water, 3% sodium hydrogensulfite
distillationSolvent was distilled under reduced pressure
temperatureafter cooling to ambient temperature
additiondichloromethane was added

Sources & evidence

ORD record: ord-064b02659be145d8826c945c2233ee9f
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07517988B2

Reaction notes

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