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

HRID 1454439Notes

Reaction equation

HRID 1454439 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]([CH2:28][CH2:29][CH2:30][CH3:31])=[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]([CH2:28][CH2:29][CH2:30][CH3:31])=[CH:24][CH:23]=2)=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 6422Trifluoroacetic acidHCID 433378442-(4-Bromophenyl)-1-(4-butylphenyl)ethan-1-one

Product 1

HCID 575306121-bromo-4-[(Z)-2-chloro-2-(4-butylphenyl) vinyl] benzeneYield 95%

Procedure

To a 2 L three-necked flask containing TFA (231 mL, 3.01 mol) and acetyl chloride (171.4 mL, 2.41 mol) was added in one portion 2-(4-bromophenyl)-1-(4-butylphenyl) ethanone (Ve) (100 g; 0.301 mol) at RT. The reaction mixture was stirred at room temperature overnight and work-up was then similar with those described above. The title compound (m=100 g) was obtained in a 95% yield. Melting point: 59-61° C.

Sources & evidence

ORD record
ord-3747d2493b0c480f9c2c92428d2f28bd
Source dataset
uspto-grants-2009_01
Patent number
US07479575B2

Reaction notes

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