Potassium Carbonate → [5-(4-Chloro-benzoxy)-4'-trifluoromethyl-biphenyl-3-yl]-acetic acid ethyl ester

HRID 1169950Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:23])[CH2:5][C:6]1[CH:7]=[C:8]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)[CH:9]=[C:10]([OH:12])[CH:11]=1)[CH3:2].C([O-])([O-])=O.[K+].[K+].[Cl:30][C:31]1[CH:38]=[CH:37][C:34]([CH2:35]Br)=[CH:33][CH:32]=1>CC#N>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][C:6]1[CH:7]=[C:8]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:21])([F:22])[F:20])=[CH:15][CH:14]=2)[CH:9]=[C:10]([O:12][CH2:35][C:34]2[CH:37]=[CH:38][C:31]([Cl:30])=[CH:32][CH:33]=2)[CH:11]=1)[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of (5-hydroxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester (70 mg, 0.22 mmol), K2CO3 (60 mg, 2.0 equivalents), 4-chlorobenzyl bromide (50 mg, 1.1 equivalents) in MeCN (2 mL) was heated at 80° C. for 2 hours. The resultant suspension was filtered and evaporated to dryness. The residue was purified by flash column chromatography (EtOAc:petroleum ether) to give 85 mg (83%) [5-(4-chloro-benzoxy)-4′-trifluoromethyl-biphenyl-3-yl]-acetic acid ethyl ester as a clear oil.

Workup

filtrationThe resultant suspension was filtered
customevaporated to dryness
customThe residue was purified by flash column chromatography (EtOAc:petroleum ether)

Sources & evidence

ORD record: ord-76c7332b320447f7a739ac4313bfd83d
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07825160B2

Reaction notes

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