Hydrogen Bromide → Methyl 2-bromo-2-(3-fluorophenyl)acetate

HRID 1044042Notes

Reaction equation

HRID 1044042 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=1.[Br:13]N1C(=O)CCC1=O.Br>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[Br:13][CH:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1)[C:9]([O:11][CH3:12])=[O:10]

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 67184N-bromobutanimideHCID 2734108Methyl 3-fluorophenylacetate

Product 1

HCID 57495616Methyl 2-bromo-2-(3-fluorophenyl)acetateYield 96%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

Methyl 2-(3-fluorophenyl)acetate (1.90 g, 11.3 mmol) and N-bromo succinimide (2.01 g, 11.3 mmol) were dissolved in CCl4 (80 ml). HBr (64 ul, 0.56 mmol) was added, and the mixture was stirred under reflux overnight. The mixture was cooled at room temperature, diluted with DCM, and washed with sat. NaHCO3, water and brine. The organic layer was dried (Na2SO4), filtered, and evaporated obtaining intermediate I15 (2.68 g, 96% yield).

Workup

  1. temperatureunder reflux overnight
  2. washwashed with sat. NaHCO3, water and brine
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customobtaining intermediate I15 (2.68 g, 96% yield)

Sources & evidence

ORD record
ord-6feb96ab08bc4bf7ae345ccae01b3d8c
Source dataset
uspto-grants-2013_10
Patent number
US08563577B2

Reaction notes

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