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

HRID 483749Notes

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

Participants

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

temperatureThe reaction mixture was heated at the reflux temperature for 90 minutes
filtrationfiltered
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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