N-bromobutanimide → 4-(bromomethyl)-N-tert-butyl-2-methoxybenzamide

HRID 536542Notes

Reaction equation

HRID 536542 reaction equation
[C:1]([NH:5][C:6](=[O:16])[C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:8]=1[O:14][CH3:15])([CH3:4])([CH3:3])[CH3:2].[Br:17]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.ClCCl>[Br:17][CH2:13][C:10]1[CH:11]=[CH:12][C:7]([C:6]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:16])=[C:8]([O:14][CH3:15])[CH:9]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 11435975N-tert-Butyl-2-methoxy-4-methylbenzamide

Product 1

HCID 674226894-(bromomethyl)-N-tert-butyl-2-methoxybenzamide

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

An amount of 160 mg (0.72 mmol) of the compound from Example 22A was heated under reflux with 129 mg (0.72 mmol) of N-bromosuccinimide and also 12 mg (0.07 mmol) of 2,2′-azobis-2-methylpropanenitrile in 5 ml of carbon tetrachloride for 16 h. After cooling to RT, the mixture was diluted with 10 ml of dichloromethane and washed with 10 ml of water. It was dried over sodium sulphate, filtered and concentrated under reduced pressure. The crude product was subsequently purified by chromatography [Method 8]. This gave 103 mg (47% of theory) of the target compound.

Workup

  1. washwashed with 10 ml of water
  2. dry with materialIt was dried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was subsequently purified by chromatography [Method 8]

Sources & evidence

ORD record
ord-ad4281443bf240c49ee3e15572709942
Source dataset
uspto-grants-2014_10
Patent number
US08859601B2

Reaction notes

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