N-bromobutanimide → Methyl 2-bromo-2-(3-fluorophenyl)acetate

HRID 1255053Notes

Reaction equation

HRID 1255053 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>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl.Br>[CH3:12][O:11][C:9](=[O:10])[CH:8]([Br:13])[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1

Participants

6

Reactant 2

HCID 67184N-bromobutanimideHCID 2734108Methyl 3-fluorophenylacetate

Product 1

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

Reagents, catalysts & solvents 3

HCID 260Hydrogen BromideCatalystHCID 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) are dissolved in CCl4 (80 mL). HBr (64 ul, 0.56 mmol) is added and the mixture is stirred under reflux overnight. The mixture is cooled at RT, diluted with DCM and washed with sat. NaHCO3, water and brine. The organic layer is dried (Na2SO4), filtered and evaporated obtaining intermediate I144 as a yellow oil (2.68 g, 96% yield).

Workup

  1. temperatureunder reflux overnight
  2. washwashed with sat. NaHCO3, water and brine
  3. dry with materialThe organic layer is dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-07a329881da9437091501e9413d8c9cc
Source dataset
uspto-grants-2013_06
Patent number
US08455646B2

Reaction notes

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