Carbon tetrabromide → (e)-n-[4-(3-Bromo-propyl)-3-chloro-phenyl]-3-(2-chloro-4-trifluoromethyl-phenyl)-acrylamide

HRID 898555Notes

Reaction equation

HRID 898555 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:20][C:21]1[CH:22]=[C:23]([NH:31][C:32](=[O:46])/[CH:33]=[CH:34]/[C:35]2[CH:40]=[CH:39][C:38]([C:41]([F:44])([F:43])[F:42])=[CH:37][C:36]=2[Cl:45])[CH:24]=[CH:25][C:26]=1[CH2:27][CH2:28][CH2:29]O.[Br:47]C(Br)(Br)Br>ClCCl>[Br:47][CH2:29][CH2:28][CH2:27][C:26]1[CH:25]=[CH:24][C:23]([NH:31][C:32](=[O:46])/[CH:33]=[CH:34]/[C:35]2[CH:40]=[CH:39][C:38]([C:41]([F:44])([F:43])[F:42])=[CH:37][C:36]=2[Cl:45])=[CH:22][C:21]=1[Cl:20]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 68878212(e)-n-[3-Chloro-4-(3-hydroxy-propyl)-phenyl]-3-(2-chloro-4-trifluoromethyl-phenyl)-acrylamide

Product 1

HCID 87610233(e)-n-[4-(3-Bromo-propyl)-3-chloro-phenyl]-3-(2-chloro-4-trifluoromethyl-phenyl)-acrylamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.577 g (2.200 mmol) triphenylphosphine was added batchwise to a suspension of 0.836 g (2.000 mmol) (E)-N-[3-chloro-4-(3-hydroxy-propyl)-phenyl]-3-(2-chloro-4-trifluoromethyl-phenyl)-acrylamide and 0.730 g (2.200 mmol) tetrabromomethane in 10 mL dichloromethane and the mixture was stirred for 48 h at RT. The reaction mixture was purified by column chromatography (silica gel, dichloromethane) and the residue was triturated with petroleum ether.

Workup

  1. customThe reaction mixture was purified by column chromatography (silica gel, dichloromethane)
  2. customthe residue was triturated with petroleum ether

Sources & evidence

ORD record
ord-beab3948de0142909c82ae7a8854c65e
Source dataset
uspto-grants-2008_04
Patent number
US07351719B2

Reaction notes

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