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

HRID 1748153Notes

Reaction equation

HRID 1748153 reaction equation
[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[O:15][C:16]([F:19])([F:18])[F:17])[C:5]=2[CH2:20]O)[CH2:3][CH2:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:42]>ClCCl>[Br:42][CH2:20][C:5]1[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][C:16]([F:19])([F:18])[F:17])=[N:7][O:8][C:4]=1[CH:1]1[CH2:3][CH2:2]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]isoxazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Into a 100 mL round bottom flask was placed (5-cyclopropyl-3-(2-(trifluoromethoxy)phenyl)isoxazol-4-yl)-methanol (4 g, 13.3 mmol), triphenylphosphine (5.6 g, 20 mmol, 1.5 equiv) and dichloromethane (40 mL). The mixture was stirred until completely dissolved, and then slowly cannulated dropwise into a stirring solution of carbon tetrabromide (6.6 g, 20 mmol, 1.5 eq) in dichloromethane (20 ml). The mixture was stirred for one hour and the solvent was then evaporated in vacuo. The crude residue was purified by silica gel chromatography using a 0-50% gradient of ethyl acetate/hexane. The desired product was obtained as a colorless oil. MS m/z 361.9/363.9 (M+1, Br79/Br81 isotope pattern).

Workup

  1. customInto a 100 mL round bottom flask was placed
  2. dissolutionuntil completely dissolved
  3. stirringThe mixture was stirred for one hour
  4. customthe solvent was then evaporated in vacuo
  5. customThe crude residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-857b145d9c454ffabe6ec7464900db02
Source dataset
uspto-grants-2015_10
Patent number
US09150568B2

Reaction notes

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