Phosphorus tribromide → 5-(Bromomethyl)-3-dodecylisoxazole

HRID 1756961Notes

Reaction equation

HRID 1756961 reaction equation
[CH2:1]([C:13]1[CH:17]=[C:16]([CH2:18]O)[O:15][N:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].P(Br)(Br)[Br:21]>ClCCl>[Br:21][CH2:18][C:16]1[O:15][N:14]=[C:13]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH:17]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 106355535-Isoxazolemethanol, 3-dodecyl-

Product 1

HCID 105443765-(Bromomethyl)-3-dodecylisoxazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred, chilled (+3° C.) solution of 3-dodecyl-5-isoxazole methanol (1.0 g, 0.0037 mol) in dichloromethane (20 mL) was added in one portion phosphorous tribromide (0.13 mL, 0.0014 mol), and the solution was stirred at +3° C. for 1.5 hours, then at room temperature for 3 days. The mixture was washed carefully with saturated sodium bisulfite, saturated sodium bicarbonate, and saturated sodium chloride. The organic layer was dried (MgSO4) and rotoevaporated to a yellow oil which solidified upon standing; yield 1.12 g (93%); mp 31.5°-35° C.

Workup

  1. waitat room temperature for 3 days
  2. washThe mixture was washed carefully with saturated sodium bisulfite, saturated sodium bicarbonate, and saturated sodium chloride
  3. dry with materialThe organic layer was dried (MgSO4)

Sources & evidence

ORD record
ord-76e732fc9223406bb6c9d8a669bf2356
Source dataset
uspto-grants-1995_08
Patent number
US05441975

Reaction notes

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