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

HRID 1255090Notes

Reaction equation

HRID 1255090 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH3:12])=[O:10].[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:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1]

Participants

6

Reactant 2

HCID 67184N-bromobutanimideHCID 2733230Methyl 2-fluorophenylacetate

Product 1

HCID 18004644Methyl 2-bromo-2-(2-fluorophenyl)acetateYield 100%

Reagents, catalysts & solvents 3

HCID 260Hydrogen BromideCatalystHCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 2-(2-fluorophenyl)acetate (1.0 g, 5.95 mmol) in CCl4 (15 mL), are added N-bromo succinimide (1.06 g, 5.95 mmol) and 48% hydrogen bromide (33 uL, 0.30 mmol) and the reaction is refluxed for 15 hours. Reaction is diluted with DCM and washed with Na2CO3 and water. The organic phase is dried over Na2SO4, filtered and evaporated under vacuum to afford intermediate I261 as a dark brown oil (1.47 g, quantitative yield).

Workup

  1. temperaturethe reaction is refluxed for 15 hours
  2. customReaction
  3. washwashed with Na2CO3 and water
  4. dry with materialThe organic phase is dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-00c0266630d54085bd1d4b1b7331e30b
Source dataset
uspto-grants-2013_06
Patent number
US08455646B2

Reaction notes

Loading…