2-Bromo-1-(4-(difluoromethoxy)phenyl)ethan-1-one → Methyl 4-[4-(4-difluoromethoxyphenyl)-2-thiazolyl]benzoate

HRID 1264931Notes

Reaction equation

[C:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)(=[S:3])[NH2:2].[F:14][CH:15]([F:27])[O:16][C:17]1[CH:26]=[CH:25][C:20]([C:21](=O)[CH2:22]Br)=[CH:19][CH:18]=1>C(O)C>[F:14][CH:15]([F:27])[O:16][C:17]1[CH:26]=[CH:25][C:20]([C:21]2[N:2]=[C:1]([C:4]3[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=3)[S:3][CH:22]=2)=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of methyl 4-thiocarbamoylbenzoate (1.56 g), 4-difluoromethoxyphenacyl bromide (2.65 g) and ethanol (15 ml) was stirred at 80 to 90° C. for 1 hour. The reaction mixture was cooled, and precipitated crystals were collected by filtration to obtain methyl 4-[4-(4-difluoromethoxyphenyl)-2-thiazolyl]benzoate (2.00 g, yield: 69%). The product was recrystallized from ethanol to obtain pale yellow prisms. Melting Point: 146 to 148° C.

Workup

temperatureThe reaction mixture was cooled
customprecipitated crystals
filtrationwere collected by filtration

Sources & evidence

ORD record: ord-346d8df8b0ea4483ba4a9805e04c7ca0
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06545009B1

Reaction notes

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