(NE)-N-[(4-bromo-3-methylphenyl)methylidene]hydroxylamine → HCID 118046969, compound

HRID 63877Notes

Reaction equation

HRID 63877 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[N:9]/[OH:10])=[CH:4][C:3]=1[CH3:11].[Cl:12][C:13]1[CH:18]=[C:17]([C:19]([C:21]([F:24])([F:23])[F:22])=[CH2:20])[CH:16]=[C:15]([Cl:25])[C:14]=1[F:26].Cl([Na])=O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:20][C:19]([C:17]3[CH:16]=[C:15]([Cl:25])[C:14]([F:26])=[C:13]([Cl:12])[CH:18]=3)([C:21]([F:24])([F:23])[F:22])[O:10][N:9]=2)=[CH:4][C:3]=1[CH3:11]

Participants

5

Reactant 3

HCID 21833735(NE)-N-[(4-bromo-3-methylphenyl)methylidene]hydroxylamineHCID 584682331,3-Dichloro-2-fluoro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzeneHCID 178521654HCID 178521654, compound

Product 1

HCID 118046969HCID 118046969, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Into a 50-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed dichloromethane (10 mL), (E)-N-[(4-bromo-3-methylphenyl)methylidene]hydroxylamine (50 mg, 0.23 mmol, 1.00 equiv), 1,3-dichloro-2-fluoro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (60 mg, 0.23 mmol, 1.00 equiv), chlorosylsodium (5 mL). The resulting solution was stirred overnight at room temperature. The resulting solution was diluted with 50 mL of DCM. The resulting mixture was washed with 3×10 mL of brine. The organic phase was dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 82 mg (75%) of 3-(4-bromo-3-methylphenyl)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazole as a white solid.

Workup

  1. customInto a 50-mL round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. washThe resulting mixture was washed with 3×10 mL of brine
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThis resulted in 82 mg (75%) of 3-(4-bromo-3-methylphenyl)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazole as a white solid

Sources & evidence

ORD record
ord-49d98bb8092f4964a6da6d10735e8f9b
Source dataset
uspto-grants-2016_09
Patent number
US09447084B2

Reaction notes

Loading…