Carbon tetrabromide → 4-(Bromomethyl)-5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]isoxazole

HRID 250278Notes

Reaction equation

HRID 250278 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:20]1([C:23]2[O:27][N:26]=[C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[O:34][C:35]([F:38])([F:37])[F:36])[C:24]=2[CH2:39]O)[CH2:22][CH2:21]1.C(Br)(Br)(Br)[Br:42]>ClCCl>[Br:42][CH2:39][C:24]1[C:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[O:34][C:35]([F:38])([F:37])[F:36])=[N:26][O:27][C:23]=1[CH:20]1[CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 669061975-Cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-4-isoxazolemethanol

Product 1

HCID 669060924-(Bromomethyl)-5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]isoxazoleYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triphenylphosphine (1.1 equiv., 51.5 mmoles, 13.5 g) is added in small portions to a 0° C. solution of [5-Cyclopropyl-3-(2-trifluoromethoxy-phenyl)-isoxazol-4-yl]-methanol and carbon tetrabromide (1.1 equiv, 51.5 mmoles, 17.1 g) in dichloromethane (187.1 mL). The reaction mixture is stirred at ambient temperature for 15 h and concentrated under reduced pressure. The crude residue is purified via silica gel chromatography eluting with 5:1 hexanes/ethyl acetate) to afford the title compound (15 g, 88%) as a white powder.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe crude residue is purified via silica gel chromatography
  3. washeluting with 5:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-7cefa366799940cdb816c3484cbc9dce
Source dataset
uspto-grants-2011_01
Patent number
US07863302B2

Reaction notes

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