Propionyl chloride → 4-(3-Bromopropylthio)phenylpropan-1-one

HRID 1722837Notes

Reaction equation

HRID 1722837 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][S:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:12](Cl)(=[O:15])[CH2:13][CH3:14].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[Br:1][CH2:2][CH2:3][CH2:4][S:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:15])[CH2:13][CH3:14])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 62324Propionyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 70618473-Bromopropyl phenyl sulfide

Product 1

HCID 146502814-(3-Bromopropylthio)phenylpropan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of thioether from Example 1, (460 g, 2 moles) and propionyl chloride (202 g, 2.2 moles) in dichloromethane (8 L) at -15° C. was added in portions of approximately 30 g over 1 hour, aluminum chloride (320 g, 2.4 moles). After two hours at -15° C. the reaction mixture was quenched with ice until it became colorless. 1N HCl (2 L) was added and the reaction mixture was stirred until two clear phases were obtained (approximately 30 minutes). The organic layer was siphoned off and dried (Na2SO4). Evaporation afforded an oil which crystallized upon addition of hexane (2 L) and cooling in ice water bath; yield 470 g, m.p. 40°-41° C.

Workup

  1. customAfter two hours at -15° C. the reaction mixture was quenched with ice until it
  2. addition1N HCl (2 L) was added
  3. customwere obtained (approximately 30 minutes)
  4. dry with materialdried (Na2SO4)
  5. customEvaporation
  6. customafforded an oil which
  7. customcrystallized upon addition of hexane (2 L)
  8. temperaturecooling in ice water bath

Sources & evidence

ORD record
ord-9c0f3f7046344989b041d75962298cf3
Source dataset
uspto-grants-1989_08
Patent number
US04857659

Reaction notes

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