(3-Fluoropropyl)triphenylphosphonium bromide → HCID 178506025, compound

HRID 863371Notes

Reaction equation

[Br-].[F:2][CH2:3][CH2:4][CH2:5][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC([O-])(C)C.[K+].[F:31][C:32]1[CH:33]=[C:34]([C@H:39]2[CH2:44][CH2:43][C@H:42]([C@H:45]3[CH2:50][CH2:49][C@H:48]([CH:51]=O)[CH2:47][CH2:46]3)[CH2:41][CH2:40]2)[CH:35]=[CH:36][C:37]=1[F:38]>C1COCC1>[F:2][CH2:3][CH2:4][CH:5]=[CH:51][C@H:48]1[CH2:49][CH2:50][C@H:45]([C@H:42]2[CH2:43][CH2:44][C@H:39]([C:34]3[CH:35]=[CH:36][C:37]([F:38])=[C:32]([F:31])[CH:33]=3)[CH2:40][CH2:41]2)[CH2:46][CH2:47]1

Participants

Conditions

Temperature: -20 °C

Procedure

A mixture of (3-fluoropropyl)triphenylphosphonium bromide (13.8 g, 34.1 millimols) with THF (60 ml) was cooled down to -20° C., followed by adding t-BuOK (3.5 g, 34.1 millimols) to the mixture, stirring for one hour, dropwise adding to the mixture, a THF (120 ml) solution of trans-4-(trans-4-(3,4-difluorophenyl)cyclohexyl)cyclohexanecarbaldehyde (9.5 g, 31.0 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 reaction product in the same manner as in Example 2, to obtain raw (trans-4-(trans-4-(4-fluorobutenyl)cyclohexyl)cyclohexyl)-3,4-difluorobenzene (9.2 g).

Workup

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

Sources & evidence

ORD record: ord-4100b9d2e78b487c9483354e21bb4d70
Source dataset: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05720899

Reaction notes

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