Dichloromethane → HCID 118046905, compound

HRID 63851Notes

Reaction equation

HRID 63851 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[N:9]/[OH:10])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].ClCCl.[Cl:18][C:19]1[CH:24]=[C:23]([C:25]([C:27]([F:30])([F:29])[F:28])=[CH2:26])[CH:22]=[C:21]([C:31]([F:34])([F:33])[F:32])[CH:20]=1.[O-]Cl.[Na+]>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:26][C:25]([C:23]3[CH:22]=[C:21]([C:31]([F:32])([F:33])[F:34])[CH:20]=[C:19]([Cl:18])[CH:24]=3)([C:27]([F:30])([F:29])[F:28])[O:10][N:9]=2)=[CH:4][C:3]=1[C:11]([F:12])([F:13])[F:14]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 23665760Sodium HypochloriteHCID 86654468HCID 86654468, compoundHCID 118046913(NE)-N-[[4-bromo-3-(trifluoromethyl)phenyl]methylidene]hydroxylamine

Product 1

HCID 118046905HCID 118046905, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a 50-mL round-bottom flask, was placed (E)-N-[[4-bromo-3-(trifluoromethyl)phenyl]methylidene]hydroxylamine (1.5 g, 5.60 mmol, 1.00 equiv), dichloromethane (20 mL), 1-chloro-3-(trifluoromethyl)-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (1.6 g, 5.83 mmol, 1.10 equiv), NaOCl (10 mL). The resulting solution was stirred for 2 h at room temperature. The resulting solution was diluted with 30 mL of H2O. The resulting solution was extracted with 3×50 mL of dichloromethane and the organic layers combined. The resulting mixture was washed with 3×50 mL of brine. The mixture was dried over anhydrous sodium sulfate. The solids were filtered out. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:100). This resulted in 1.7 g (56%) of 3-[4-bromo-3-(trifluoromethyl)phenyl]-5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazole as a light yellow solid.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. extractionThe resulting solution was extracted with 3×50 mL of dichloromethane
  3. washThe resulting mixture was washed with 3×50 mL of brine
  4. dry with materialThe mixture was dried over anhydrous sodium sulfate
  5. filtrationThe solids were filtered out
  6. concentrationThe resulting mixture was concentrated under vacuum
  7. customThis resulted in 1.7 g (56%) of 3-[4-bromo-3-(trifluoromethyl)phenyl]-5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazole as a light yellow solid

Sources & evidence

ORD record
ord-a7ba6a442adc43b2bbeb94ef9c884f1a
Source dataset
uspto-grants-2016_09
Patent number
US09447084B2

Reaction notes

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