Methanol → Ethyl (4'-methylbiphenyl-2-yl)acetate

HRID 1171882Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].C(=O)([O-])[O-].[Na+].[Na+].[CH3:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1.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.C(OCC)(=O)C.O.C1(C)C=CC=CC=1>[CH3:20][C:21]1[CH:26]=[CH:25][C:24]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a mixture composed of 243.1 mg (1 mmol) of ethyl 2-(2-bromophenyl)acetate, 3.7 ml of toluene, 57.8 mg (0.05 mmol) of tetrakis(triphenylphosphine)palladium and 127.2 mg (1.2 mmol) of anhydrous sodium carbonate are added 169.9 mg (1.25 mmol) of 4-methylphenylboronic acid, followed by addition of 2.21 ml (0.055 mmol) of methanol. The reaction medium is heated at 85° C. for 16 hours with stirring. After cooling, 10 ml of water and 8 ml of ethyl acetate are added with stirring, and the mixture is then filtered through a fluted filter paper. The organic phase is recovered and the aqueous phase is extracted again with ethyl acetate.

Workup

temperatureAfter cooling
stirringwith stirring
filtrationthe mixture is then filtered through
filtrationa fluted filter paper
customThe organic phase is recovered
extractionthe aqueous phase is extracted again with ethyl acetate

Sources & evidence

ORD record: ord-59a9caae248d43a8abbb9a25d5b4f2aa
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07829721B2

Reaction notes

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