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

HRID 77020Notes

Reaction equation

HRID 77020 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-e85f4a0398c44f798c1040d3a2b1bb1c
Source dataset
uspto-grants-2014_09
Patent number
US08835682B2

Reaction notes

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