Cesium carbonate → 1,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene

HRID 1037079Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[C:6]([Cl:8])[CH:7]=1.Br[C:13]([C:15]([F:18])([F:17])[F:16])=[CH2:14].C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1.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:1][C:2]1[CH:3]=[C:4]([C:13]([C:15]([F:18])([F:17])[F:16])=[CH2:14])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 3,5-dichlorophenylboronic acid (3.8 g, 20.0 mmol), 2-bromo-3,3,3-trifluoro-prop-1-ene (4.9 g, 28 mmol), Cs2CO3 (20 mL, 2 M, 40 mmol) and Pd(PPh3)2Cl2 (421 mg) in THF (30 mL) was heated at 70° C. in a sealed tube for 4 h. The mixture was cooled to rt and partitioned between ether and H2O. The aqueous layer was extracted with EA and the combined organic layers were dried over Na2SO4. The solvent was removed under reduced pressure and the crude product was purified by column chromatography over silica gel eluted with hexanes to give 1,3-dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (3.85 g; yield 80%). 1H NMR (500 MHz, CDCl3): δ 7.41 (s, 1H), 7.35 (s, 2H), 6.06 (s, 1 H), 5.83 (s, 1 H) ppm.

Workup

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

Sources & evidence

ORD record: ord-2719f458349b478aba08f382bdefd33e
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546357B2

Reaction notes

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