Potassium Carbonate → Ethyl 4''-chloro-2''-[(phenylmethyl)oxy]-1,1':2',1''-terphenyl-2-carboxylate

HRID 269590Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[C:22]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CCOCC.O.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>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:2]2[C:3]([C:8]3[C:9]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=3)=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:22]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:21]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of ethyl 2′-bromo-2-biphenylcarboxylate (153 mg, 0.5 mmol), {4-chloro-2-[(phenylmethyl)oxy]phenyl}boronic acid (144 mg, 0.55 mmol), potassium carbonate (552 mg, 4 mmol) and tetrakis(triphenylphosphine)palladium(0) (58 mg, 0.05 mmol) was stirred and heated at 90° C. under nitrogen for 18 hours. After cooling the mixture was diluted with ether/water and the organic phase dried (magnesium sulphate), evaporated and chromatographed on silica eluting with ethyl acetate/iso-hexane (1:19) to give 104 mg of colourless gum.

Workup

temperatureAfter cooling the mixture
dry with materialthe organic phase dried (magnesium sulphate)
customevaporated
customchromatographed on silica eluting with ethyl acetate/iso-hexane (1:19)

Sources & evidence

ORD record: ord-15bf3bb09d18422f822d7c9eac780b29
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07446222B2

Reaction notes

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