Phosphorus tribromide → HCID 66678783, compound

HRID 1025972Notes

Reaction equation

HRID 1025972 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:7]=[C:6]([CH2:8]O)[O:5][N:4]=1.[Br:12]P(Br)Br>CN(C)C=O>[Br:12][CH2:8][C:6]1[O:5][N:4]=[C:3]([C:2]([F:11])([F:10])[F:1])[CH:7]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 133079935-Isoxazolemethanol,3-(trifluoromethyl)-(9CI)

Product 1

HCID 66678783HCID 66678783, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (3-(trifluoromethyl)isoxazol-5-yl)methanol (2.5 g, 15 mmol) in dimethylformamide (25 mL) was added drop wise tribromophosphine (4.64 g 17.1 mmol, 1.15 eq) and the mixture was stirred at 0° C. for 15 min and at ambient temperature for 2 h. The reaction mixture was partitioned between 10% sodium bicarbonate and dichloromethane. The phases were separated and the organic phase was washed with water and passed over a plug of silica eluting with dichloromethane. The UV active product fractions were collected and evaporated to yield the title compound as colorless oil (2.04 g 59.3%), MS 229 and 231(M)+.

Workup

  1. customThe reaction mixture was partitioned between 10% sodium bicarbonate and dichloromethane
  2. customThe phases were separated
  3. washthe organic phase was washed with water
  4. customThe UV active product fractions were collected
  5. customevaporated

Sources & evidence

ORD record
ord-a9c93eb233354a8dbc882469cf305b9a
Source dataset
uspto-grants-2014_05
Patent number
US08729105B2

Reaction notes

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