Bromine → alpha-Bromo-3-chloropropiophenone

HRID 1931033Notes

Reaction equation

HRID 1931033 reaction equation
[Br:1]Br.[Cl:3][C:4]1[CH:5]=[C:6]([C:10](=[O:13])[CH2:11][CH3:12])[CH:7]=[CH:8][CH:9]=1>C(Cl)(Cl)Cl.C(Cl)Cl>[Br:1][CH:11]([CH3:12])[C:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([Cl:3])[CH:5]=1)=[O:13]

Participants

5

Reactant 2

HCID 24408BromineHCID 5871283'-Chloropropiophenone

Product 1

HCID 4992116alpha-Bromo-3-chloropropiophenoneYield 60%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Bromine (6.07 ml, 0.12 mol) was added to a solution of 3′-chloropropiophenone (20 g, 0.12 mol) in chloroform (250 ml) at room temperature. The reaction was followed by TLC in DCM. When all of the starting material was consumed the mixture was washed with a saturated solution of sodium bicarbonate. The organic phase was dried over magnesium sulphate, filtered and evaporated. Recrystallisation from chloroform gives the desired compound in 60% yield as a pale yellow solid (18 g, 73 mmol).

Workup

  1. customWhen all of the starting material was consumed the mixture
  2. washwas washed with a saturated solution of sodium bicarbonate
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customRecrystallisation from chloroform

Sources & evidence

ORD record
ord-d1a1e3f74a65454bae9e59bf11a89515
Source dataset
uspto-grants-2012_05
Patent number
US08188150B2

Reaction notes

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