Hexane → HCID 54461430, compound

HRID 1383262Notes

Reaction equation

HRID 1383262 reaction equation
[Br-].[F:2][CH2:3][CH2:4][CH2:5][CH2:6][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[F:32][C:33]1[CH:34]=[C:35]([CH:38]=[CH:39][CH:40]=1)[CH:36]=O.CCCCCC>O1CCCC1>[F:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH:36][C:35]1[CH:34]=[C:33]([F:32])[CH:40]=[CH:39][CH:38]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 680093-FluorobenzaldehydeHCID 21187190HCID 21187190, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 54461430HCID 54461430, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 4-fluorobutyltriphenylphosphonium bromide 273 g (660 mmol) and tetrahydrofuran (abbreviated THF hereinafter) 1000 ml, potasium-tert-butoxide 88 g (684 mmol) was added under ice cooling and stirred for one hour. Then, under ice cooling, a solution of 3-fluorobenzaldehyde 74 g (596 mmol) in THF 200 ml was added dropwise, and the mixture was stirred for one hour at room temperature. The reaction mixture was poured into hexane 1000 ml, and the crystals deposited were filtered off. The filtrate was concentrated, and distilled (93° C./6 mmHg) to obtain 3-(5-fluoro-1-pentenyl)fluorobenzene 86 g. (Yield:79.6%).

Workup

  1. additionwas added under ice cooling
  2. stirringthe mixture was stirred for one hour at room temperature
  3. filtrationthe crystals deposited were filtered off
  4. concentrationThe filtrate was concentrated
  5. distillationdistilled (93° C./6 mmHg)

Sources & evidence

ORD record
ord-31c581bab57c4f888a57347c0c22c347
Source dataset
uspto-grants-2001_07
Patent number
US06254941B1

Reaction notes

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