Boron tribromide → 2-(5-Oxazolyl)phenol

HRID 1581788Notes

Reaction equation

HRID 1581788 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[O:17][CH:16]=[N:15][CH:14]=1>ClCCl>[O:17]1[C:13]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[OH:6])=[CH:14][N:15]=[CH:16]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 167406765-(2-Methoxyphenyl)-1,3-oxazole

Product 1

HCID 227234652-(5-Oxazolyl)phenolYield 114.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Boron tribromide (1M in dichloromethane, 36 ml) is added slowly to a cold solution (0° C.) of the above oxazole (3.0 g, 17.1 mmol) in dichloromethane (215 ml). After stirring over night at room temperature, ice-water (50 ml) is added carefully. The aqueous layer is extracted with dichloromethane (50 ml), and the combined organic layers are dried over sodium sulfate and concentrated under reduced pressure. The precipitate which formed after addition of dichloromethane (70 ml) is collected by filtration, heated with dichloromethane (15 ml), and filtered again to give 3.16 g of 2-(5-oxazolyl)phenol. This phenolic product is reacted with (2S)-glycidyl 3-nitrobenzenesulfonate substantially as described for Epoxide 1 to give 400 mg of the title epoxide (9.5%).

Workup

  1. extractionThe aqueous layer is extracted with dichloromethane (50 ml)
  2. dry with materialthe combined organic layers are dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe precipitate which formed
  5. filtrationis collected by filtration
  6. temperatureheated with dichloromethane (15 ml)
  7. filtrationfiltered again

Sources & evidence

ORD record
ord-1ed16a3a2c6d4a3cb2696d0a38ba72bd
Source dataset
uspto-grants-2004_05
Patent number
US06730792B2

Reaction notes

Loading…