Water → HCID 178477916, compound

HRID 1716797Notes

Reaction equation

HRID 1716797 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH2:9]([O:16][C:17]1[CH:22]=[C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:20]([Cl:31])=[CH:19][C:18]=1[C:32]1[CH:36]=[CH:35][NH:34][N:33]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O>ClCCl>[CH2:9]([O:16][C:17]1[CH:22]=[C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:20]([Cl:31])=[CH:19][C:18]=1[C:32]1[C:36]([Br:1])=[CH:35][NH:34][N:33]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 178477876HCID 178477876, compound

Product 1

HCID 178477916HCID 178477916, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Bromosuccinimide (4.70 g, 26 mmol) was added in portions over 5 minutes to a stirred solution of 3-(2,4-Bis-benzyloxy-5-chloro-phenyl)-1H-pyrazole (10.29 g 26 mmol) in dichloromethane (200 ml). The reaction mixture was stirred at ambient temperature for 2 hours then water (200 ml) was added and vigorous stirring continued for 10 minutes. The phases were separated and the organic phase was washed with water (3×100 ml), saturated aqueous sodium chloride solution (2×100mi) and dried over sodium sulphate. The mixture was filtered and filtrate solvents were removed in vacuo to afford an off-white solid, which was triturated with ethyl acetate/hexane (1:20) mixture to give 3-(2,4-Bis-benzyloxy-5-chloro-phenyl)-4-bromo-1H-pyrazole (11.80 g, 97%) as off-white solid.

Workup

  1. stirringvigorous stirring
  2. waitcontinued for 10 minutes
  3. customThe phases were separated
  4. washthe organic phase was washed with water (3×100 ml), saturated aqueous sodium chloride solution (2×100mi)
  5. dry with materialdried over sodium sulphate
  6. filtrationThe mixture was filtered
  7. customfiltrate solvents were removed in vacuo
  8. customto afford an off-white solid, which
  9. customwas triturated with ethyl acetate/hexane (1:20) mixture

Sources & evidence

ORD record
ord-d069296435684b068ed8317b16817b1b
Source dataset
uspto-grants-2010_09
Patent number
US07803831B2

Reaction notes

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