1-Naphthalenecarboxaldehyde, 4-bromo-, oxime → HCID 118046649, compound

HRID 63872Notes

Reaction equation

HRID 63872 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](/[CH:12]=[N:13]/[OH:14])=[CH:4][CH:3]=1.[Cl:15][C:16]1[CH:21]=[C:20]([C:22]([C:24]([F:27])([F:26])[F:25])=[CH2:23])[CH:19]=[C:18]([C:28]([F:31])([F:30])[F:29])[CH:17]=1.Cl([Na])=O>ClCCl>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH2:23][C:22]([C:20]3[CH:19]=[C:18]([C:28]([F:29])([F:30])[F:31])[CH:17]=[C:16]([Cl:15])[CH:21]=3)([C:24]([F:27])([F:26])[F:25])[O:14][N:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 230800341-Naphthalenecarboxaldehyde, 4-bromo-, oximeHCID 86654468HCID 86654468, compoundHCID 178521654HCID 178521654, compound

Product 1

HCID 118046649HCID 118046649, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 250-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed dichloromethane (100 mL), (E)-N-[(4-bromonaphthalen-1-yl)methylidene]hydroxylamine (4.5 g, 17.99 mmol, 1.00 equiv), 1-chloro-3-(trifluoromethyl)-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (4.9 g, 17.84 mmol, 1.00 equiv), chlorosylsodium (30 mL). The resulting solution was stirred overnight at room temperature. The aqueous layer was extracted with 3×20 mL of dichloromethane and the organic layers combined and washed with 3×40 mL of brine. The organic phase was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column and washed with ethyl acetate/petroleum ether (1/10-1/5). This resulted in 7.1 g (75%) of 3-(4-bromonaphthalen-1-yl)-5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazole as a off-white solid.

Workup

  1. customInto a 250-mL round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. extractionThe aqueous layer was extracted with 3×20 mL of dichloromethane
  4. washwashed with 3×40 mL of brine
  5. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under vacuum
  7. washwashed with ethyl acetate/petroleum ether (1/10-1/5)
  8. customThis resulted in 7.1 g (75%) of 3-(4-bromonaphthalen-1-yl)-5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazole as a off-white solid

Sources & evidence

ORD record
ord-8a285cb8632d462aafd4b1713cf0a6f2
Source dataset
uspto-grants-2016_09
Patent number
US09447084B2

Reaction notes

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