N-bromobutanimide → 135660-93-4

HRID 77057Notes

Reaction equation

HRID 77057 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 18004644135660-93-4Yield 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-f26078ed0dd84d4fbbbb137db6d9c9c3
Source dataset
uspto-grants-2014_09
Patent number
US08835682B2

Reaction notes

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