Acetyl chloride → 1-bromo-4-[(Z)-2-chloro-2-(4-chlorophenyl) vinyl] benzene

HRID 1454435Notes

Reaction equation

HRID 1454435 reaction equation
C(O)(C(F)(F)F)=O.C([Cl:11])(=O)C.[Br:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=O)=[CH:15][CH:14]=1>>[Br:12][C:13]1[CH:18]=[CH:17][C:16](/[CH:19]=[C:20](\[Cl:11])/[C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 6422Trifluoroacetic acidHCID 149017782-(4-Bromophenyl)-1-(4-chlorophenyl)ethanone

Product 1

HCID 575306171-bromo-4-[(Z)-2-chloro-2-(4-chlorophenyl) vinyl] benzeneYield 74.5%

Procedure

In a 250 mL flask, TFA (24.7 mL; 322.8 mmol) and acetyl chloride (18.34 mL; 258.23 mmol) were added in one portion into 2-(4-bromophenyl)-1-(4-chlorophenyl) ethanone (Vd) (10.0 g; 32.30 mmol) at RT. Protocol and work-up was then similar with those described above. The title compound (m=7.89 g) was obtained in a 74.5% yield. Melting point: 108° C.

Sources & evidence

ORD record
ord-99dc0cf1963b4131bb45b7d5deea406e
Source dataset
uspto-grants-2009_01
Patent number
US07479575B2

Reaction notes

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