Bromoacetyl bromide → HCID 86647191, compound

HRID 1038536Notes

Reaction equation

HRID 1038536 reaction equation
[CH2:1]([O:8][C:9]([C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[C:20](/[CH:30]=[CH:31]\[CH3:32])[CH:19]=1)([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:33][CH2:34][C:35](Br)=[O:36]>ClCCl>[CH2:1]([O:8][C:9]([C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][N:27]([C:35](=[O:36])[CH2:34][Br:33])[CH2:26][CH2:25]2)=[C:20](/[CH:30]=[CH:31]\[CH3:32])[CH:19]=1)([C:10]([F:12])([F:13])[F:11])[C:14]([F:15])([F:16])[F:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 61147Bromoacetyl bromide2×HCID 86647190(Z)-1-{4-[2-(benzyloxy)-1,1,1,3,3,3-hexafluoropropan-2-yl]-2-(prop-1-en-1-yl)phenyl}piperazine

Product 1

HCID 86647191HCID 86647191, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(Z)-1-{4-[2-(benzyloxy)-1,1,1,3,3,3-hexafluoropropan-2-yl]-2-(prop-1-en-1-yl)phenyl}piperazine (38 mg, 0.0595 mmol) was dissolved in dichloromethane (1.0 mL). Under ice-cold conditions, N,N′-dimethylaniline (9.0 μL, 0.0714 mmol) and bromoacetylbromide (5.5 μL, 0.0625 mmol) were added, and the mixture was stirred under ice-cold conditions for 0.5 hours. Then, under ice-cold conditions, N,N′-dimethylaniline (9.0 μL, 0.0714 mmol) and bromoacetylbromide (5.5 μL, 0.0625 mmol) were added, and the mixture was stirred under ice-cold conditions for 0.5 hours. The reaction solution was concentrated in vacuo, and the obtained residue was purified by silica-gel column chromatography (hexane/acetone). The title compound (16 mg (yield 47%)) was obtained as a yellow oil.

Workup

  1. stirringthe mixture was stirred under ice-cold conditions for 0.5 hours
  2. concentrationThe reaction solution was concentrated in vacuo
  3. customthe obtained residue was purified by silica-gel column chromatography (hexane/acetone)

Sources & evidence

ORD record
ord-d24531caa7e44d06821cdf36f61389ea
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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