Potassium Carbonate → Methyl (4'-hydroxybiphenyl-3-yl)acetate

HRID 2247446Notes

Reaction equation

CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)O1.Br[C:18]1[CH:19]=[C:20]([CH2:24][C:25]([O:27][CH3:28])=[O:26])[CH:21]=[CH:22][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.C(OCC)(=O)C.[Pd].ClC1[C-](P)C(C2C=CC=CC=2)=C(C2C=CC=CC=2)C=1Cl.[CH-]1C=CC=C1.[Fe+2]>[OH:15][C:12]1[CH:11]=[CH:10][C:9]([C:22]2[CH:23]=[CH:18][CH:19]=[C:20]([CH2:24][C:25]([O:27][CH3:28])=[O:26])[CH:21]=2)=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 70 °C

Procedure

10 g of 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)phenol and 12.5 g of methyl 3-bromophenylacetate were dissolved in 150 ml of 1,2-dimethoxyethane, then 14 g of potassium carbonate and 920 mg of dichlorodiphenyl phosphinoferrocene palladium were added thereto, and the mixture was stirred overnight at 70° C. in a nitrogen atmosphere. The reaction mixture was diluted with ethyl acetate and washed with 1N hydrochloric acid. The organic layer was dried over anhydrous magnesium sulfate and then filtered, and the filtrate was concentrated. The residue was purified by silica gel column chromatography, to give 10.336 g of the title compound in the 2:1 hexane-ethyl acetate fraction.

Workup

washwashed with 1N hydrochloric acid
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
filtrationfiltered
concentrationthe filtrate was concentrated
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-78e8d93d603e49c2bc5b378c16cee729
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687664B2

Reaction notes

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