2,3-Dichloropropene → HCID 86621043, compound

HRID 226100Notes

Reaction equation

HRID 226100 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[SH:11])([CH3:4])([CH3:3])[CH3:2].[Cl:12][C:13]([CH2:15]Cl)=[CH2:14].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11][CH2:15][C:13]([Cl:12])=[CH2:14])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 65652,3-DichloropropeneHCID 11430Potassium CarbonateHCID 27950322-tert-butylbenzenethiol

Product 1

HCID 86621043HCID 86621043, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 2-tert-butyl-benzenethiol (5.0 g, 24.09 mmol) in acetone (25 mL) is reacted with 2,3-dichloro-propene (2.2 mL, 24.09 mmol) and K2CO3 (4.3 g, 31.32 mmol) at reflux overnight. It is cooled to rt and filtered and washed with EtOAc, and concentrated. The crude material is purified by chromatography gives the title compound (5.66 g, 23.58 mmol, 98%). 1H NMR (CDCl3): δ 1.52 (s, 9H), 3.77 (s, 2H), 5.27 (bs, 1H), 5.31 (bs, 1H), 7.11-7.20 (m, 2H), 7.36-7.43 (m, 1H) ppm. ES-MS (m/z): calcd for C13H17CIS M+: 240.8. found: 240.9.

Workup

  1. temperatureat reflux overnight
  2. filtrationfiltered
  3. washwashed with EtOAc
  4. concentrationconcentrated
  5. customThe crude material is purified by chromatography

Sources & evidence

ORD record
ord-970fa7968891444ba33de139fdef997e
Source dataset
uspto-grants-2009_07
Patent number
US07557103B2

Reaction notes

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