Potassium Carbonate → Methyl 3'-hydroxy-2,6,2'-trimethylbiphenyl-4-carboxylate

HRID 2307559Notes

Reaction equation

HRID 2307559 reaction equation
COC[O:4][C:5]1[C:6]([CH3:14])=[C:7](B(O)O)[CH:8]=[CH:9][CH:10]=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[C:6]([CH3:14])=[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:8]=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11849880Methyl 3,5-dimethyl-4-(((trifluoromethyl)sulfonyl)oxy)benzoateHCID 226069353-Methoxymethoxy-2-methylbenzene-1-boronic acid

Product 1

HCID 22606880Methyl 3'-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 1.5 g (7.6 mmol) of 3-methoxymethoxy-2-methylbenzene-1-boronic acid (described in Example 11(c)) with 2 g (6.4 mmol) of methyl 3,5-dimethyl-4-trifluoromethanesulphonyloxybenzoate, 7.7 mL of 2.0M potassium carbonate solution and 370 mg (0.32 mmol) of tetrakis(triphenylphosphine)palladium, followed by deprotection in methanol, the desired product is obtained in the form of a white solid (m.p.=149° C.; m=1.34 g; Y=67%).

Sources & evidence

ORD record
ord-e56c1a12b8c44b7283cb59879015e6dd
Source dataset
uspto-grants-2004_12
Patent number
US06831106B1

Reaction notes

Loading…