Cesium carbonate → HCID 86685080, compound

HRID 1750832Notes

Reaction equation

[Cl:1][C:2]1[C:3]([F:19])=[C:4](B2OC(C)(C)C(C)(C)O2)[CH:5]=[C:6]([Cl:9])[C:7]=1[F:8].Br[C:21]([C:23]([F:26])([F:25])[F:24])=[CH2:22].C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:9][C:6]1[CH:5]=[C:4]([C:21]([C:23]([F:26])([F:25])[F:24])=[CH2:22])[C:3]([F:19])=[C:2]([Cl:1])[C:7]=1[F:8]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 2-(3,5-dichloro-2,4-difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (7.34 g, 23.75 mmol), 2-bromo-3,3,3-trifluoroprop-1-ene (5.82 g, 33.25 mmol), Cs2CO3 (15.5 g, 47.5 mmol) and Pd(PPh3)2Cl2 (400 mg) in THF (30 mL) and water (15 mL) was heated at 70° C. in a sealed tube for 4 h under argon. The mixture was cooled to rt and partitioned between EA and H2O. The aqueous layer was extracted with EA and the combined organic layers were dried over Na2SO4. The solvent was removed and the residue was purified by column chromatography on silica gel eluted with hexanes to give crude compound of 1,3-dichloro-2,4-difluoro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (3.93 g) as a colorless oil. It was used in next step without further purification.

Workup

temperatureThe mixture was cooled to rt
custompartitioned between EA and H2O
extractionThe aqueous layer was extracted with EA
dry with materialthe combined organic layers were dried over Na2SO4
customThe solvent was removed
customthe residue was purified by column chromatography on silica gel
washeluted with hexanes

Sources & evidence

ORD record: ord-a36580f4115d4da4af8bd34bfdad51c8
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156860B2

Reaction notes

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