Phosphorus tribromide → 7-(Bromomethyl)-3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazole

HRID 1506325Notes

Reaction equation

HRID 1506325 reaction equation
[C:1]1([C:7]2[O:11][N:10]=[C:9]([C:12]3[O:16][N:15]=[C:14]4[C:17]5[C:22]([CH2:23][CH2:24][C:13]=34)=[CH:21][C:20]([CH2:25]O)=[CH:19][CH:18]=5)[C:8]=2[C:27]([F:30])([F:29])[F:28])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Br)(Br)[Br:32]>ClCCl>[Br:32][CH2:25][C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][CH:19]=1)[C:14]1=[N:15][O:16][C:12]([C:9]3[C:8]([C:27]([F:28])([F:29])[F:30])=[C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[O:11][N:10]=3)=[C:13]1[CH2:24][CH2:23]2

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 67171626HCID 67171626, compound

Product 1

HCID 671678437-(Bromomethyl)-3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazoleYield 71.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)methanol (Preparation 6B, 700 mg, 1.698 mmol) in anhydrous dichloromethane (25 mL) was added phosphorous tribromide (0.240 mL, 2.55 mmol) slowly at 0° C. under nitrogen. The reaction mixture was then stirred at room temperature overnight. Next, 10 mL of ice water was added at 0° C. to quench the reaction. The organic layer was separated, washed with saturated aqueous sodium bicarbonate solution (20 mL) and filtered over CELITE®. The aqueous layer was separated, combined with the aqueous layer from before and extracted with dichloromethane (2×20 mL). The combined organic solutions were dried over sodium sulfate, filtered through a silica gel pad that was rinsed with dichloromethane, and concentrated under reduced pressure to give 7-(bromomethyl)-3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazole (580 mg, 1.220 mmol, 71.9% yield) as a yellow solid. LC/MS M+1=477.

Workup

  1. customto quench
  2. customthe reaction
  3. customThe organic layer was separated
  4. washwashed with saturated aqueous sodium bicarbonate solution (20 mL)
  5. filtrationfiltered over CELITE®
  6. customThe aqueous layer was separated
  7. extractionextracted with dichloromethane (2×20 mL)
  8. dry with materialThe combined organic solutions were dried over sodium sulfate
  9. filtrationfiltered through a silica gel pad that
  10. washwas rinsed with dichloromethane
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-42f4b788c3264f08a3b6fa5e58db3833
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

Loading…