Phosphorus tribromide → 4-(Bromomethyl)-5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazole

HRID 1689762Notes

Reaction equation

HRID 1689762 reaction equation
[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:10]=3[Cl:16])[C:5]=2[CH2:17]O)[CH2:3][CH2:2]1.P(Br)(Br)[Br:20]>ClCCl>[Br:20][CH2:17][C:5]1[C:6]([C:9]2[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:16])=[N:7][O:8][C:4]=1[CH:1]1[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 45790382(5-Cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-yl)methanol

Product 1

HCID 593693284-(Bromomethyl)-5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazoleYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of (5-cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazol-4-yl)-methanol (0.124 g, 0.44 mmol) in dichloromethane (4 mL) is added phosphorous tribromide (0.261 g, 0.963 mmol). The ice bath is removed after 20 minutes and the reaction is allowed to stir for an additional twenty minutes at room temperature. The reaction is quenched with pH 7 buffer and is extracted with dichloromethane several times. The organic layers are combined, washed with brine, and dried over sodium sulfate. The reaction is filtered and concentrated under reduced pressure to yield the title compound (0.124 g, 82%). 1H-NMR (400 MHz CDCl3) δ 7.45-7.33 (m, 3H), 4.20 (s, 2H), 2.09 (m, 1H), 1.27 (m, 2H), 1.16 (m, 2H)

Workup

  1. customThe ice bath is removed after 20 minutes
  2. customThe reaction is quenched with pH 7 buffer
  3. extractionis extracted with dichloromethane several times
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationThe reaction is filtered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7f02df043e864b08a0ead16e08e6f656
Source dataset
uspto-grants-2012_04
Patent number
US08153624B2

Reaction notes

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