(3,3,3-Trifluoropropyl)triphenylphosphonium bromide → HCID 178509795, compound

HRID 863374Notes

Reaction equation

[Br-].[F:2][C:3]([F:26])([F:25])[CH2:4][CH2:5][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC([O-])(C)C.[K+].[C:33]([C:35]1[CH:40]=[CH:39][C:38]([C@H:41]2[CH2:46][CH2:45][C@H:44]([CH:47]=O)[CH2:43][CH2:42]2)=[CH:37][CH:36]=1)#[N:34]>C1COCC1>[F:2][C:3]([F:26])([F:25])[CH2:4][CH:5]=[CH:47][C@H:44]1[CH2:45][CH2:46][C@H:41]([C:38]2[CH:39]=[CH:40][C:35]([C:33]#[N:34])=[CH:36][CH:37]=2)[CH2:42][CH2:43]1

Participants

Conditions

Temperature: -20 °C

Procedure

A mixture of (3,3,3-trifluoropropyl)triphenylphosphonium bromide (9.0 g, 20.5 millimols) with THF (45 ml) was cooled down to -20° C., followed by adding t-BuOK (2.5 g, 22.5 millimols) to the mixture, stirring for 30 minutes, dropwise adding to the mixture, a THF (50 ml) solution of trans-4-(4-cyanophenyl)cyclohexanecarbaldehyde (4.8 g, 22.5 millimols) so as to keep the temperature at -20° C. or lower, stirring the mixture at the same temperature for 2 hours, and treating the product in the same manner as in Example 1, to obtain raw 4-(trans-4-(4,4,4-trifluorobutenyl)cyclohexyl)benzonitrile (5.1 g).

Workup

additiondropwise adding to the mixture
customat -20° C.
stirringlower, stirring the mixture at the same temperature for 2 hours
additiontreating the product in the same manner as in Example 1

Sources & evidence

ORD record: ord-7e19fdf9fa9b4fb8abd93bd25099fdcb
Source dataset: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05720899

Reaction notes

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