Thiophene-3-boronic acid → 2-(Thien-3-yl)-5-fluorophenol

HRID 1581794Notes

Reaction equation

HRID 1581794 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[OH:9].[S:10]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11]1.BrC1C=C(F)C(F)=CC=1O.S1C=CC=C1B(O)O>>[S:10]1[CH:14]=[CH:13][C:12]([C:2]2[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=2[OH:9])=[CH:11]1

Participants

5

Reactant 4

HCID 581760Thiophene-3-boronic acid2×HCID 27246002-Bromo-5-fluorophenolHCID 27339602-Thiopheneboronic acidHCID 27362882-Bromo-4,5-difluorophenol2×

Product 1

HCID 227234392-(Thien-3-yl)-5-fluorophenol

Procedure

2-Bromo-5-fluorophenol is coupled with thiophene-3-boronic acid; 2-bromo-4,5-difluorophenol is coupled with thiophene-2-boronic acid; and 2-bromo-4,5-difluorophenol is coupled with thiophene-3-boronic acid in Suzuki reactions substantially as described for Epoxide 48, to yield 2-(thien-3-yl)-5-fluorophenol; 2-(thien-2-yl)-4,5-difluorophenol; and 2-(thien-3-yl)-4,5-difluorophenol, respectively. These phenolic products are reacted with (2S)-glycidyl 3-nitrobenzenesulfonate substantially as described for Epoxide 1 to yield the title epoxides.

Sources & evidence

ORD record
ord-c039dd4972cb42bea22f3f002355498d
Source dataset
uspto-grants-2004_05
Patent number
US06730792B2

Reaction notes

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