Potassium Carbonate → Methyl 2,2'-dimethyl-1,1'-biphenyl-4-carboxylate

HRID 2244198Notes

Reaction equation

Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH3:12].[C:13]1([CH3:22])[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[CH3:12][C:3]1[CH:4]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[CH:10]=[CH:11][C:2]=1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH3:22]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of methyl 4-bromo-3-methylbenzoate (25.0 g, 110 mmol), o-tolylboronic acid (16.5 g, 120 mmol) and potassium carbonate (50 g, 360 mmol) in dioxane:water (300 mL: 200 mL) was purged with nitrogen for 1 hour. [1,1′bis(Diphenylphosphino)ferrocene]dichloropalladium[II] (4.5 g, 5.5 mmol) was added and the reaction mixture was heated to 100° C. with vigorous stirring for 3.5 hours. The cooled reaction mixture was filtered through Celite and the cake washed with ethyl acetate (500 mL). The organic phase was separated, washed with 1 M sodium hydroxide (500 mL) and brine (500 mL), dried over anhydrous potassium carbonate and concentrated in vacuo to give the crude product as a dark oil (28.6 g). Purification by flash chromatography using a solvent gradient of 2% ethyl acetate in hexane afforded the title compound (24.7 g, 93%) as a pale yellow oil.

Workup

customwater (300 mL: 200 mL) was purged with nitrogen for 1 hour
customThe cooled reaction mixture
filtrationwas filtered through Celite
washthe cake washed with ethyl acetate (500 mL)
customThe organic phase was separated
washwashed with 1 M sodium hydroxide (500 mL) and brine (500 mL)
dry with materialdried over anhydrous potassium carbonate
concentrationconcentrated in vacuo
customto give the crude product as a dark oil (28.6 g)
customPurification by flash chromatography

Sources & evidence

ORD record: ord-8c7b7d61b872469abcbaa5cca49bb36d
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07678787B2

Reaction notes

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