N-bromobutanimide → HCID 11167257, compound

HRID 2087024Notes

Reaction equation

HRID 2087024 reaction equation
[Si:1]([O:8][C:9]1[CH:10]=[C:11]([OH:24])[CH:12]=[C:13]([Cl:23])[C:14]=1[O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1C(=O)N([Br:32])C(=O)C1>CN(C=O)C.O>[Br:32][C:12]1[C:13]([Cl:23])=[C:14]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[C:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[CH:10][C:11]=1[OH:24]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 11429180HCID 11429180, compound

Product 1

HCID 11167257HCID 11167257, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 0.050 g (0.12 mmol) of 16 and 0.023 g (0.12 mmol) of NBS in 2 mL of DMF under argon was stirred at 25° C. for 1 day. The reaction mixture was diluted with 30 mL of water, extracted three times with diethyl ether (40 mL each), and the combined extracts were washed with brine (30 mL), dried (MgSO4), and concentrated to give 0.042 g (70% yield). This material was used in next step without purification. 1H NMR (CDCl3) δ 6.53 (s, 1H, Ar, C6-H), 1.03 (s, 9H, t-Bu), 0.96 (s, 9H, t-Bu), 0.22 (s, 6H, Me), 0.17 (s, 6H, Me); 13C NMR (CDCl3) δ 148.3 (s), 147.4 (s), 138.8 (s), 127.0 (s), 106.9 (d), 102.9 (s), 26.2 (q, t-Bu), 18.8 (s), −3.3 (q, Me), −3.5 (q, Me).

Workup

  1. extractionextracted three times with diethyl ether (40 mL each)
  2. washthe combined extracts were washed with brine (30 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customto give 0.042 g (70% yield)
  6. customThis material was used in next step without purification

Sources & evidence

ORD record
ord-bb3e123f325341c0b6aa502a8d2a3137
Source dataset
uspto-grants-2004_04
Patent number
US06727277B1

Reaction notes

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