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N-bromobutanimide → (2RS)-1,1,1-trifluoro-2-(4-ethoxyphenyl)-3-[(RS)-alpha-bromo-3-phenoxybenzyloxy]-propane

HRID 483749
Notes
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Reaction equation

HRID 483749 reaction equation
[Br:1]N1C(=O)CCC1=O.[F:9][C:10]([F:38])([F:37])[CH:11]([C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH3:36])=[CH:30][CH:29]=1)[CH2:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:16]=1>C(Cl)(Cl)(Cl)Cl>[F:9][C:10]([F:37])([F:38])[CH:11]([C:28]1[CH:29]=[CH:30][C:31]([O:34][CH2:35][CH3:36])=[CH:32][CH:33]=1)[CH2:12][O:13][CH:14]([Br:1])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:16]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 106695812-(4-Ethoxyphenyl)-3,3,3-trifluoropropyl 3-phenoxybenzyl ether

Product 1

HCID 19753527(2RS)-1,1,1-trifluoro-2-(4-ethoxyphenyl)-3-[(RS)-alpha-bromo-3-phenoxybenzyloxy]-propane

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
0 °C

Procedure

A catalytic amount of α,α'-azo-iso-butyronitrile was added to a solution of N-bromosuccinimide (0.14 g) and (RS)-1,1,1-trifluoro-2-(4-ethoxyphenyl)-3-(3-phenoxybenzyloxy)propane (0.3 g) in carbon tetrachloride (14 cm3). The reaction mixture was heated at the reflux temperature for 90 minutes, then cooled to 0° C., filtered, and the filtrate concentrated by evaporation under reduced pressure to leave (2RS)-1,1,1-trifluoro-2-(4-ethoxyphenyl)-3-[(RS)-α-bromo-3-phenoxybenzyloxy]-propane as a pale yellow oil which was used without further purification.

Workup

  1. temperatureThe reaction mixture was heated at the reflux temperature for 90 minutes
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-079204e5cf5f4cfd9c130bd3f8a24d46
Source dataset
uspto-grants-1993_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05225607

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes