Sodium Carbonate → 5'-Bromo-4-(ethylsulfonyl)-2'-fluoro-2-methoxy-1,1'-biphenyl

HRID 1846028Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4](I)[CH:3]=1.[CH2:10]([S:12]([C:15]1[CH:20]=[CH:19][C:18](B2OC(C)(C)C(C)(C)O2)=[C:17]([O:30][CH3:31])[CH:16]=1)(=[O:14])=[O:13])[CH3:11].C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>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>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([C:18]2[CH:19]=[CH:20][C:15]([S:12]([CH2:10][CH3:11])(=[O:14])=[O:13])=[CH:16][C:17]=2[O:30][CH3:31])[CH:3]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A suspension of 4-bromo-1-fluoro-2-iodobenzene (420 mg, 1.39 mmol), 2-(4-(ethylsulfonyl)-2-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (Preparation 21, 500 mg, 1.53 mmol), 2M aqueous sodium carbonate solution (2.5 mL) and dioxane (10 mL) was degassed with nitrogen for 30 minutes. Tetrakis(triphenylphosphine)palladium(0) (80 mg, 0.07 mmol) was added and the reaction warmed to 110° C. and stirred for 1 hour. The reaction was cooled to room temperature, diluted with water (10 mL), extracted with EtOAc (2×10 mL), dried over Na2SO4, filtered and concentrated under vacuum. The residue was purified using silica gel column chromatography eluting with heptanes/EtOAc 7/3 to afford the title compound as a pale yellow solid in 73% yield, 418 mg.

Workup

customwas degassed with nitrogen for 30 minutes
temperatureThe reaction was cooled to room temperature
extractionextracted with EtOAc (2×10 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated under vacuum
customThe residue was purified
washeluting with heptanes/EtOAc 7/3

Sources & evidence

ORD record: ord-93e455a4c28e43a1ba3ffb5abe810731
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952008B2

Reaction notes

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