N-bromobutanimide → HCID 18951130, compound

HRID 515493Notes

Reaction equation

HRID 515493 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[Br:12]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:12][CH:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)[C:9]([OH:11])=[O:10]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 74653(3-Bromophenyl)acetic acid

Product 1

HCID 18951130HCID 18951130, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 3-bromophenylacetic acid (25.0 g, 116 mmol) in carbon tetrachloride (200 ml) was added N-bromosuccinimide (22.8 g, 128 mmol) at room temperature. The mixture was refluxed for 3 hours and cooled to room temperature. The resulting precipitate was filtered off. The filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (eluant: hexane/ethyl acetate=4/1) to afford bromo-(3-bromo-phenyl)-acetic acid as yellow liquid (27.8 g, 81%).

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. filtrationThe resulting precipitate was filtered off
  3. concentrationThe filtrate was concentrated in vacuo
  4. customThe residue was purified by silica gel column chromatography (eluant: hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-1a954ff11f8f41e8ac3fb9c642f5589e
Source dataset
uspto-grants-2015_08
Patent number
US09108957B2

Reaction notes

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