Sodium borohydride → (6-Fluoro-2',6'-dimethylbiphenyl-3-yl)methanol

HRID 2426754Notes

Reaction equation

HRID 2426754 reaction equation
[BH4-].[Na+].[F:3][C:4]1[C:9]([C:10]2[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:17])=[CH:8][C:7]([CH:18]=[O:19])=[CH:6][CH:5]=1>C(O)C>[F:3][C:4]1[C:9]([C:10]2[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:17])=[CH:8][C:7]([CH2:18][OH:19])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 866328336-Fluoro-2',6'-dimethylbiphenyl-3-carbaldehyde

Product 1

HCID 57787552(6-Fluoro-2',6'-dimethylbiphenyl-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In an atmosphere of nitrogen, tetrakistriphenylphosphine palladium was added to a mixture of 2-bromo-1,3-dimethylbenzene, 2-fluoro-5-formylphenyl boronic acid, a 1 M sodium carbonate aqueous solution, ethanol and toluene, followed by stirring at 80° C. for 8 hours to obtain 6-fluoro-2′,6′-dimethylbiphenyl-3-carbaldehyde. Under cooling on an ice-methanol bath, sodium borohydride was added in small portions to an ethanol solution of the resulting 6-fluoro-2′,6′-dimethylbiphenyl-3-carbaldehyde, and the reaction mixture was stirred at the same temperature for 1 hour to obtain (6-fluoro-2′,6′-dimethylbiphenyl-3-yl)methanol.

Workup

  1. temperatureUnder cooling on an ice-methanol bath

Sources & evidence

ORD record
ord-5a4ae80d5879497184469be55d915057
Source dataset
uspto-grants-2011_06
Patent number
US07968552B2

Reaction notes

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