(3-Fluoropropyl)triphenylphosphonium bromide → HCID 178509748, compound

HRID 863372Notes

Reaction equation

HRID 863372 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+].[C:31]([C:33]1[CH:38]=[CH:37][C:36]([CH2:39][CH2:40][C@H:41]2[CH2:46][CH2:45][C@H:44]([CH:47]=O)[CH2:43][CH2:42]2)=[CH:35][CH:34]=1)#[N:32]>C1COCC1>[F:2][CH2:3][CH2:4][CH:5]=[CH:47][C@H:44]1[CH2:45][CH2:46][C@H:41]([CH2:40][CH2:39][C:36]2[CH:37]=[CH:38][C:33]([C:31]#[N:32])=[CH:34][CH:35]=2)[CH2:42][CH2:43]1

Participants

5

Reactant 3

HCID 11429580(3-Fluoropropyl)triphenylphosphonium bromideHCID 23665647Potassium tert-butoxideHCID 178509751HCID 178509751, compound

Product 1

HCID 178509748HCID 178509748, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

A mixture of (3-fluoropropyl)triphenylphosphonium bromide (14.7 g, 36.5 millimols) with THF (60 ml) was cooled down to -20° C., followed by adding t-BuOK (4.1 g, 36.5 millimols) to the mixture, stirring for one hour, dropwise adding to the mixture, a THF (50 ml) solution of trans-4-(2-(4-cyanophenyl)ethyl)cyclohexanecarbaldehyde (9.0 g, 30.2 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 except that the quantity used for extraction was made 200 ml, to obtain raw 4-(2-(trans-4-(4-fluorobutenyl)cyclohexyl)ethyl)benzonitrile (8.1 g).

Workup

  1. additiondropwise adding to the mixture
  2. customat -20° C.
  3. stirringlower, stirring the mixture at the same temperature for 2 hours
  4. additiontreating the product in the same manner as in Example 1 except that the quantity
  5. extractionused for extraction

Sources & evidence

ORD record
ord-614422abe1134a8e80c2a58222e5bcee
Source dataset
uspto-grants-1998_02
Patent number
US05720899

Reaction notes

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