Potassium Carbonate → Methyl 5'-hydroxy-2,6,2'-trimethylbiphenyl-4-carboxylate

HRID 2307566Notes

Reaction equation

HRID 2307566 reaction equation
COC[O:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7](B(O)O)[CH:6]=1.[CH3:15][C:16]1[CH:17]=[C:18]([CH:23]=[C:24]([CH3:34])[C:25]=1OS(C(F)(F)F)(=O)=O)[C:19]([O:21][CH3:22])=[O:20].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:25]2[C:24]([CH3:34])=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][C:16]=2[CH3:15])[CH:6]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11849880Methyl 3,5-dimethyl-4-(((trifluoromethyl)sulfonyl)oxy)benzoateHCID 226069385-(Methoxymethoxy)-2-methylphenylboronic acid

Product 1

HCID 22606931Methyl 5'-hydroxy-2,6,2'-trimethylbiphenyl-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 (described in Example 16(c)) with 5.3 g (17 mmol) of methyl 3,5-dimethyl-4-trifluoromethanesulphonyloxybenzoate, 17 mL of 2.0M potassium carbonate solution and 1 g (0.82 mmol) of tetrakis(triphenylphosphine)palladium, followed by deprotection in methanol, the desired product is obtained in the form of a yellow oil (m=3.0 g; Y=65%).

Sources & evidence

ORD record
ord-7b45a4de77e54c49add668961268b613
Source dataset
uspto-grants-2004_12
Patent number
US06831106B1

Reaction notes

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