Carbon tetrabromide → 5-(Bromomethyl)-3-methoxy-1,2-oxazole

HRID 1192956

Reaction equation

HRID 1192956 reaction equation
[CH3:1][O:2][C:3]1[CH:7]=[C:6]([CH2:8]O)[O:5][N:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:30]>ClCCl>[Br:30][CH2:8][C:6]1[O:5][N:4]=[C:3]([O:2][CH3:1])[CH:7]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 106782583-Methoxy-5-isoxazolemethanol

Product 1

HCID 108454055-(Bromomethyl)-3-methoxy-1,2-oxazoleYield 104%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(3-Methoxy-isoxazol-5-yl)-methanol (822 mg, 6.4 mmol) was dissolved in dichloromethane (10 ml) and triphenyl phosphine (1.84 g, 7.0 mmol) and carbon tetrabromide (2 g, 6.11 mmol) were added at 0° C. The mixture was stirred for 2 hours at 0° C. and concentrated. The crude product was purified by chromatography on silica gel (eluent: ethyl acetate/hexane) to give the product as a colourless oil (1.22 g, 99% yield) which was used in the next step without further purification.

Workup

  1. concentrationconcentrated
  2. customThe crude product was purified by chromatography on silica gel (eluent: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-24116bc5d2954304a1842115c55f4903
Source dataset
uspto-grants-2014_03
Patent number
US08680290B2

Linked notes

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