N-bromobutanimide → HCID 90397757, compound

HRID 2203460Notes

Reaction equation

HRID 2203460 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:32])=[C:6]([C:8]2[CH:9]=[CH:10][C:11]3[O:15][N:14]=[C:13]([N:16]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:12]=3[CH:31]=2)[CH:7]=1.[Br:33]N1C(=O)CCC1=O>C(#N)C>[Br:33][C:4]1[C:5]([OH:32])=[C:6]([C:8]2[CH:9]=[CH:10][C:11]3[O:15][N:14]=[C:13]([N:16]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:17]([O:19][C:20]([CH3:23])([CH3:21])[CH3:22])=[O:18])[C:12]=3[CH:31]=2)[CH:7]=[C:2]([Cl:1])[CH:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 89555358HCID 89555358, compound

Product 1

HCID 90397757HCID 90397757, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of di-tert-butyl [5-(5-chloro-2-hydroxyphenyl)-1,2-benzoxazol-3-yl]imidodicarbonate (2.00 g, 4.34 mmol) in acetonitrile (45 mL) was added N-bromosuccinimide (0.811 g, 4.56 mmol). The mixture was stirred at ambient temperature for 0.5 h and concentrated in vacuo. The residue was purified by column chromatography eluting with a 5-15% gradient of ethyl acetate in hexanes) to afford di-tert-butyl [5-(3-bromo-5-chloro-2-hydroxyphenyl)-1,2-benzoxazol-3-yl]imidodicarbonate as an orange solid in 35% yield (0.83 g): 1H NMR (300 MHz, DMSO-d6) δ 9.55 (s, 1H), 7.95-7.93 (m, 1H), 7.89-7.86 (m, 2H), 7.69 (d, J=2.6 Hz, 1H), 7.38 (d, J=2.6 Hz, 1H), 1.39 (s, 18H); MS (ES−) m/z 536.9 (M−1), 538.9 (M−1), 540.9 (M−1).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by column chromatography
  3. washeluting with a 5-15% gradient of ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-2a05384f88724be59e9876a5caece650
Source dataset
uspto-grants-2016_06
Patent number
US09365578B2

Reaction notes

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