3-Bromo-4-methoxybenzaldehyde → 4'-Fluoro-6-methoxy[1,1'-biphenyl]-3-carbaldehyde

HRID 1059160Notes

Reaction equation

HRID 1059160 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].[F:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:2]2[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[C:4]([CH:5]=[O:6])[CH:3]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 986623-Bromo-4-methoxybenzaldehydeHCID 2856454-Fluorophenylboronic acid

Product 1

HCID 223912344'-Fluoro-6-methoxy[1,1'-biphenyl]-3-carbaldehydeYield 79.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 10340Sodium CarbonateSolvent

Procedure

By the reaction in the same manner as in Example 5-(ii) using 3-bromo-p-anisaldehyde (14.0 g), 4-fluorophenylboronic acid (14.6 g), 2M aqueous sodium carbonate solution (260 ml) and tetrakis(triphenylphosphine)palladium(0) (3.76 g), the title compound (11.9 g) was obtained as white needle crystals.

Sources & evidence

ORD record
ord-fb2f766b406a478c8310a87370d04e38
Source dataset
uspto-grants-2003_02
Patent number
US06518257B1

Reaction notes

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