N-bromobutanimide → HCID 11157507, compound

HRID 2087026Notes

Reaction equation

HRID 2087026 reaction equation
[Si:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[CH:12]=[C:11]([Cl:23])[C:10]=1[O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1C(=O)N([Br:39])C(=O)C1>CN(C=O)C.O>[Br:39][C:12]1[C:13]([O:15][Si:16]([C:19]([CH3:20])([CH3:21])[CH3:22])([CH3:18])[CH3:17])=[CH:14][C:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2])=[C:10]([O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:26])[CH3:27])[C:11]=1[Cl:23]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 11168019HCID 11168019, compound

Product 1

HCID 11157507HCID 11157507, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 0.100 g (0.20 mmol) of 14 and 0.0354 g (0.20 mmol) of NBS in 2 mL of DMF under argon was stirred at 50° C. for 2 day. The solution was diluted with 30 mL of water, extracted three times with diethyl ether (30 mL each), and the combined extracts were washed with brine, dried (MgSO4), concentrated, and column chromatographed on silica gel using a mixture of hexane and diethyl ether (100:1) as eluent to give 31.4 mg (27% yield) of 4 and 62.9 mg (54% yield) of 15. Compound 15: 1H NMR (CDCl3) δ 6.54 (s, 1H, Ar, C6-H), 1.03 (s, 18H, t-Bu), 0.97 (s, 9H, t-Bu), 0.23 (s, 12H, Me), 0.17 (s, 6H, Me).

Workup

  1. extractionextracted three times with diethyl ether (30 mL each)
  2. washthe combined extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customcolumn chromatographed on silica gel using
  6. additiona mixture of hexane and diethyl ether (100:1) as eluent

Sources & evidence

ORD record
ord-d3ac92c09d2444bc9617bcd4664e901a
Source dataset
uspto-grants-2004_04
Patent number
US06727277B1

Reaction notes

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