Ethanol → 6-Fluoro-2',6'-dimethylbiphenyl-3-carbaldehyde

HRID 2426753Notes

Reaction equation

HRID 2426753 reaction equation
Br[C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:9].[F:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]=[O:18])=[CH:13][C:12]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>C1(C)C=CC=CC=1>[F:10][C:11]1[C:12]([C:2]2[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=2[CH3:9])=[CH:13][C:14]([CH:17]=[O:18])=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 684712-Bromo-m-xyleneHCID 2763240(2-Fluoro-5-formylphenyl)boronic acid

Product 1

HCID 866328336-Fluoro-2',6'-dimethylbiphenyl-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

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.

Sources & evidence

ORD record
ord-2524ed38694b444ca59a5156f2446b32
Source dataset
uspto-grants-2011_06
Patent number
US07968552B2

Reaction notes

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