4-Bromo-1,1-difluorobut-1-ene → 4,4-Difluorobut-3-enyl thioacetate

HRID 618189

Reaction equation

HRID 618189 reaction equation
[C:1]([O-:4])(=[S:3])[CH3:2].[K+].Br[CH2:7][CH2:8][CH:9]=[C:10]([F:12])[F:11]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:1]([O:4][CH2:7][CH2:8][CH:9]=[C:10]([F:12])[F:11])(=[S:3])[CH3:2]

Participants

4

Reactant 2

HCID 27822404-Bromo-1,1-difluorobut-1-eneHCID 23670855Potassium ethanethioate

Product 1

HCID 538607444,4-Difluorobut-3-enyl thioacetateYield 38.9%

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Procedure

Potassium thioacetate (1.98 g), 4-bromo-1,1-difluorobut-1-ene (3.0 g) and tetra-n-butylammonium bromide (0.3 g, catalyst) were stirred at the ambient temperature under nitrogen for 5 hours and stored for 18 hours. The mixture was distilled using a Kugelrohr apparatus to give 4,4-difluorobut-3-enyl thioacetate as a colourless liquid (1.12 g); 1H NMR; δ 2.25(2H,m); 2.30(3H,s); 2.90(2H,t); 4.20(1H,m); (bp 115° C. at 120 mmHg).

Workup

  1. distillationThe mixture was distilled

Sources & evidence

ORD record
ord-558c03d7f31842ddaf8c340c0ad0e533
Source dataset
uspto-grants-1999_09
Patent number
US05952359

Linked notes

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