Potassium Carbonate → Methyl 4'-hydroxy-2-methylbiphenyl-4-carboxylate

HRID 2307584Notes

Reaction equation

HRID 2307584 reaction equation
COC[O:4][C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1.Br[C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][C:16]=1[CH3:24].[C:25](=O)([O-])[O-].[K+].[K+]>CO.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[OH:4][C:5]1[CH:6]=[CH:7][C:8]([C:15]2[CH:23]=[CH:22][C:18]([C:19]([O:21][CH3:25])=[O:20])=[CH:17][C:16]=2[CH3:24])=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 821314-Bromo-3-methylbenzoic acidHCID 27625284-(Methoxymethoxy)phenylboronic acid

Product 1

HCID 22606882Methyl 4'-hydroxy-2-methylbiphenyl-4-carboxylate

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 887MethanolSolvent

Procedure

In a manner similar to that of Example 1(h), by reaction of 1.61 g (8.7 mmol) of 4-methoxymethoxy-phenylboronic acid and 1.8 g (9.7 mmol) of 4-bromo-3-methylbenzoic acid with 26.7 mL of 2.0M potassium carbonate and 1.54 g of tetrakis(triphenylphosphine)-palladium, followed by deprotection-esterification in methanol, the desired product is obtained in the form of a colourless oil (m=2.06 g; Y=98%).

Sources & evidence

ORD record
ord-8b5b5604de864ac6ac2b1eb53ac440b8
Source dataset
uspto-grants-2004_12
Patent number
US06831106B1

Reaction notes

Loading…