Ethyl Acetate → HCID 59660650, compound

HRID 1694642Notes

Reaction equation

HRID 1694642 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([C:9]2[O:13][N:12]=[C:11]([CH2:14]O)[CH:10]=2)[CH:6]=[CH:7][CH:8]=1.C(Br)(Br)(Br)[Br:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C>C(Cl)Cl>[Br:19][CH2:14][C:11]1[CH:10]=[C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:17])([F:16])[F:1])[CH:4]=2)[O:13][N:12]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 57800077HCID 57800077, compound

Product 1

HCID 59660650HCID 59660650, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of {5-[3-(trifluoromethyl)phenyl]isoxazol-3-yl}methane-1-ol (0.28 g, 1.15 mmol) and carbon tetrabromide (0.5 g, 1.5 mmol) in methylene chloride (10 mL) at 0° C. was added dropwise a solution of triphenylphosphine (0.41 g, 1.58 mmol) in methylene chloride (5 mL). The resulting mixture was stirred at 0° C. for 1 hour, then the reaction mixture poured into ethyl acetate and Hexanes (ethyl acetate:Hexanes=1:4, 50 mL). The resulting suspension was filtered through a thin layer of silica gel and washed with ethyl acetate and Hexanes (ethyl acetate:Hexanes=1:4). The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:Hexanes=1:4) to afford 3-(bromomethyl)-5-[3-(trifluoromethyl)phenyl]isoxazole.

Workup

  1. filtrationThe resulting suspension was filtered through a thin layer of silica gel
  2. washwashed with ethyl acetate and Hexanes (ethyl acetate:Hexanes=1:4)
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate:Hexanes=1:4)

Sources & evidence

ORD record
ord-b3f3d5129e5e4c64b500a9bc72cec52d
Source dataset
uspto-grants-2012_04
Patent number
US08158810B2

Reaction notes

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