Water → HCID 58497922, compound

HRID 1505282Notes

Reaction equation

HRID 1505282 reaction equation
[Br:1][C:2](Br)=[N:3][OH:4].[Cl:6][C:7]1[CH:12]=[C:11]([C:13]([C:15]([F:18])([F:17])[F:16])=[CH2:14])[CH:10]=[C:9]([Cl:19])[CH:8]=1.C(=O)(O)[O-].[Na+].O>C(OCC)(=O)C>[Br:1][C:2]1[CH2:14][C:13]([C:11]2[CH:10]=[C:9]([Cl:19])[CH:8]=[C:7]([Cl:6])[CH:12]=2)([C:15]([F:16])([F:18])[F:17])[O:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 27632191-bromo-N-hydroxymethanecarbonimidoyl bromideHCID 231598231,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene

Product 1

HCID 58497922HCID 58497922, compoundYield 65.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of dibromoformaldoxime (6.23 g, Tetrahedron Lett., 1984, 487) in ethyl acetate (150 ml) was added 1,3-dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (6.3 g, prepared according to WO 2005/085216) and sodium bicarbonate (9.5 g). The reaction was stirred at room temperature for 96 h. Water was added, then the two layers were then separated. The aqueous layer was extracted with ethyl acetate and the combined organic layers were dried over sodium sulfate and concentrated to afford a white solid (6.23 g). 1H-NMR (CDCl3, 400 MHz): 7.47-7.43 (m, 3H), 3.95 (d, 1H), 3.58 (d, 1H)

Workup

  1. customthe two layers were then separated
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. dry with materialthe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6ff939c8e4f94997a8ca68c4051dd9a2
Source dataset
uspto-grants-2015_12
Patent number
US09216973B2

Reaction notes

Loading…