Potassium Carbonate → Methyl 5'-hydroxy-2,2'-dimethylbiphenyl-4-carboxylate

HRID 2307564Notes

Reaction equation

HRID 2307564 reaction equation
COC[O:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7](B(O)O)[CH:6]=1.Br[C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:17]=1[CH3:26].C(=O)([O-])[O-].[K+].[K+]>CO.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>[OH:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:17]=2[CH3:26])[CH:6]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 3294148Methyl 4-bromo-3-methylbenzoateHCID 226069385-(Methoxymethoxy)-2-methylphenylboronic acid

Product 1

HCID 22606936Methyl 5'-hydroxy-2,2'-dimethylbiphenyl-4-carboxylate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolvent

Procedure

In a manner similar to that of Example 11(d), by reaction of 3.7 g (18.8 mmol) of 4-methoxymethoxy-1-methylbenzene-2-boronic acid with 3.9 g (17 mmol) of methyl 4-bromo-3-methylbenzoate, 17 mL of 2.0M potassium carbonate solution and 1 mg (0.85 mmol) of tetrakis(triphenylphosphine)palladium, followed by deprotection in methanol, the desired product is obtained in the form of a thick, colourless oil (m=2.87 mg; Y=51%).

Sources & evidence

ORD record
ord-cc3929331349499b92f37fc425334461
Source dataset
uspto-grants-2004_12
Patent number
US06831106B1

Reaction notes

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