N-bromobutanimide → Benzoic acid, 4-bromo-2-(bromomethyl)-5-fluoro-, methyl ester

HRID 1778754Notes

Reaction equation

HRID 1778754 reaction equation
[Br:1][C:2]1[C:11]([F:12])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:13])[CH:3]=1.[Br:14]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:1][C:2]1[C:11]([F:12])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH2:13][Br:14])[CH:3]=1

Participants

6

Reactant 2

HCID 67184N-bromobutanimideHCID 56965486Methyl 4-bromo-5-fluoro-2-methylbenzoate

Product 1

HCID 86722851Benzoic acid, 4-bromo-2-(bromomethyl)-5-fluoro-, methyl esterYield 92%

Reagents, catalysts & solvents 3

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of methyl 4-bromo-5-fluoro-2-methylbenzoate (1.0 g, 4.0 mmol) (Ellanoval Laboratories Cat. No. 38-0304), N-bromosuccinimide (900. mg, 5.06 mmol) and benzoyl peroxide (50 mg, 0.2 mmol) in carbon tetrachloride (50 mL) was refluxed under a nitrogen atmosphere for 4 h. After cooling the mixture was diluted with methylene chloride. The organic solution was washed with brine, then dried over Na2SO4. After filtration the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%) to afford the desired product (1.2 g).

Workup

  1. temperatureAfter cooling the mixture
  2. washThe organic solution was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration the filtrate
  5. concentrationwas concentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%)

Sources & evidence

ORD record
ord-86fab34a200342bca443c837844284fe
Source dataset
uspto-grants-2016_02
Patent number
US09266892B2

Reaction notes

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