N-bromobutanimide → HCID 86672776, compound

HRID 1755009Notes

Reaction equation

HRID 1755009 reaction equation
[Br:1]N1C(=O)CCC1=O.[C:9]([O:13][C:14](=[O:27])[N:15]([C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[C:18]=1[O:25][CH3:26])[CH3:16])([CH3:12])([CH3:11])[CH3:10]>ClCCl>[C:9]([O:13][C:14](=[O:27])[N:15]([C:17]1[CH:22]=[C:21]([CH3:23])[C:20]([Br:1])=[C:19]([CH3:24])[C:18]=1[O:25][CH3:26])[CH3:16])([CH3:12])([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 66817530HCID 66817530, compound

Product 1

HCID 86672776HCID 86672776, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-Bromosuccinimide (326 mg, 1.83 mmol) was added to a solution of (2-methoxy-3,5-dimethyl-phenyl)-methyl-carbamic acid tert-butyl ester (456 mg, 1.72 mmol) in dichloromethane (1.8 ml) at 0° C., and the mixture was stirred at room temperature for 50 minutes. The reaction mixture was diluted with dichloromethane and adjusted to pH 9 and washed with water and a 1 N aqueous NaOH solution (1 ml), and the organic layer was dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give (4-bromo-2-methoxy-3,5-dimethyl-phenyl)-methyl-carbamic acid tert-butyl ester as a colorless solid (545 mg, 92%).

Workup

  1. washwashed with water
  2. dry with materiala 1 N aqueous NaOH solution (1 ml), and the organic layer was dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-2af111c0bf994ed1a8122e273bbb9b0f
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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