N-bromobutanimide → HCID 58160243, compound

HRID 1425591Notes

Reaction equation

HRID 1425591 reaction equation
[C:1]([O:4][C:5]1[CH:17]=[CH:16][C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]=2[CH:6]=1)(=[O:3])[CH3:2].C1C(=O)N([Br:25])C(=O)C1>C(Cl)Cl>[C:1]([O:4][C:5]1[CH:17]=[CH:16][C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([Br:25])[CH:13]=3)[NH:8][C:7]=2[CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 11816968HCID 11816968, compound

Product 1

HCID 58160243HCID 58160243, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 9H-carbazol-2-yl acetate (500 mg, 2.2 mmol) in DCM (40 mL) was added a solution of NBS in 25 mL of DCM dropwise at rt. The reaction mixture was stirred in the dark for 5 h. It was washed with water (3×50 mL) and dried over MgSO4 and concentrated. The crude product was purified by silica chromatography (EtOAc/hexane) to afford 6-bromo-9H-carbazol-2-yl acetate (WZ02025) as an off-white solid (250 mg, containing 17% dibrominated product). MS (ESI) m/z 305 (M+H+).

Workup

  1. washIt was washed with water (3×50 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe crude product was purified by silica chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-df1c68543d884150aa3a7ba5d1bb5d73
Source dataset
uspto-grants-2015_01
Patent number
US08932557B2

Reaction notes

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