Bromine → HCID 54254433, compound

HRID 2248962Notes

Reaction equation

HRID 2248962 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:8](=[S:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[Cl-].[Al+3].[Cl-].[Cl-].[Br:15]Br>C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[C:8](=[S:10])[CH2:9][Br:15]

Participants

5

Reactant 3

HCID 24408BromineHCID 6451240Aluminum(III) ChlorideHCID 19995233HCID 19995233, compound

Product 1

HCID 54254433HCID 54254433, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

m-Methylthioacetophenone (7.14 g, 43 mmol) was dissolved in chloroform (100 ml). Aluminium chloride (catalytic amount) and bromine (2.2 ml, 43 mmol) were added and stirred for 1 h. The reaction was quenched with aqueous sodium chloride-sodium bicarbonate and the organic layer separated, dried (MgSO4) and evaporated under reduced pressure. The residue was taken up in ethyl acetate, washed with aqueous sodium bicarbonate, then brine, dried (MgSO4) and evaporated under reduced pressure to yield m-Methylthiophenacyl bromide (7.64 g, 73%); δH(CDCl3) 7.1-7.9(4H,m, aryl), 4.40(2H,S,CH2), 2.45(3H,S,SCH3H).

Workup

  1. customThe reaction was quenched with aqueous sodium chloride-sodium bicarbonate
  2. customthe organic layer separated
  3. dry with materialdried (MgSO4)
  4. customevaporated under reduced pressure
  5. washwashed with aqueous sodium bicarbonate
  6. dry with materialbrine, dried (MgSO4)
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-5dd1965029e144f38dd05f7b31a57354
Source dataset
uspto-grants-1991_08
Patent number
US05041567

Reaction notes

Loading…