HCID 86654468, compound → 3-[4-Bromo-3-(2,2,2-trifluoroethyl)phenyl]-5-[3-chloro-5-(trifluoromethyl)phenyl]-4,5-dihydro-1,2-oxazole

HRID 63864Notes

Reaction equation

HRID 63864 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([C:10](F)(F)F)=C)[CH:5]=[C:4]([C:14]([F:17])([F:16])[F:15])[CH:3]=1.[Br:18][C:19]1[CH:24]=[CH:23][C:22]([CH:25]=[N:26][OH:27])=[CH:21][C:20]=1[CH2:28][C:29]([F:32])([F:31])[F:30]>ClCCl.[O-]Cl.[Na+]>[Br:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH2:10][CH:8]([C:6]3[CH:5]=[C:4]([C:14]([F:15])([F:16])[F:17])[CH:3]=[C:2]([Cl:1])[CH:7]=3)[O:27][N:26]=2)=[CH:21][C:20]=1[CH2:28][C:29]([F:30])([F:31])[F:32]

Participants

5

Reactant 2

HCID 86654468HCID 86654468, compoundHCID 131737209HCID 131737209, compound

Product 1

HCID 1180469173-[4-Bromo-3-(2,2,2-trifluoroethyl)phenyl]-5-[3-chloro-5-(trifluoromethyl)phenyl]-4,5-dihydro-1,2-oxazole

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 23665760Sodium HypochloriteSolvent

Procedure

Into a 100-mL round-bottom flask, was placed 1-chloro-3-(trifluoromethyl)-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (680 mg, 2.48 mmol, 1.00 equiv), a solution of N-[[4-bromo-3-(2,2,2-trifluoroethyl)phenyl]methylidene]hydroxylamine (700 mg, 2.48 mmol, 1.10 equiv) in dichloromethane (20 mL), NaClO (10 mL). The resulting solution was stirred overnight at room temperature. The reaction was then quenched by the addition of 10 mL of water. The resulting solution was extracted with 3×20 mL of dichloromethane and the organic layers combined. The resulting mixture was washed with 3×20 mL of brine. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:30-1:10). This resulted in 600 mg (50%) of 3-[4-bromo-3-(2,2,2-trifluoroethyl)phenyl]-5-[3-chloro-5-(trifluoromethyl)phenyl]-4,5-dihydro-1,2-oxazole as yellow oil.

Workup

  1. customInto a 100-mL round-bottom flask, was placed
  2. customThe reaction was then quenched by the addition of 10 mL of water
  3. extractionThe resulting solution was extracted with 3×20 mL of dichloromethane
  4. washThe resulting mixture was washed with 3×20 mL of brine
  5. concentrationThe resulting mixture was concentrated under vacuum
  6. customThis resulted in 600 mg (50%) of 3-[4-bromo-3-(2,2,2-trifluoroethyl)phenyl]-5-[3-chloro-5-(trifluoromethyl)phenyl]-4,5-dihydro-1,2-oxazole as yellow oil

Sources & evidence

ORD record
ord-60918547806c4f6bb226db00c2d23777
Source dataset
uspto-grants-2016_09
Patent number
US09447084B2

Reaction notes

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