N-bromobutanimide → methyl 4-(bromomethyl)-2-fluorobenzoate

HRID 2103434Notes

Reaction equation

HRID 2103434 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:5]=1[F:11].[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][Br:13])=[CH:6][C:5]=1[F:11]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 18759805Methyl 2-fluoro-4-methylbenzoate

Product 1

HCID 18759821methyl 4-(bromomethyl)-2-fluorobenzoateYield 82%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-fluoro-4-methyl-benzoic acid methyl ester (1.12 g, 6.66 mmol) in carbon tetrachloride (12 mL) add N-bromosuccinimide (1.18 g, 6.66 mmol) and benzoyl peroxide (10 mg). Heat the resulting mixture to 60° C. for 15 hours then concentrate under vacuum to half and filter. Concentrate the filtrate under vacuum and purify the resulting crude product by flash chromatography on silica gel (eluting with 5/1 heptane/ethyl acetate) to give the title compound (1.35 g) as a white solid.

Workup

  1. concentrationthen concentrate under vacuum to half
  2. filtrationfilter
  3. concentrationConcentrate the filtrate under vacuum
  4. custompurify the resulting crude product by flash chromatography on silica gel (eluting with 5/1 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-c95e88884a4540ab9f658d1ce64bcb22
Source dataset
uspto-grants-2009_08
Patent number
US07576109B2

Reaction notes

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