Methanol → HCID 68856340, compound

HRID 2099935Notes

Reaction equation

HRID 2099935 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:19]=[CH:18][C:10]([C:11]([C:13]2[CH:17]=[CH:16][O:15][N:14]=2)=[O:12])=[CH:9][CH:8]=1.CO>ClCCl>[OH:6][C:7]1[CH:19]=[CH:18][C:10]([C:11]([C:13]2[CH:17]=[CH:16][O:15][N:14]=2)=[O:12])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 57289826HCID 57289826, compound

Product 1

HCID 68856340HCID 68856340, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

9.2 ml of boron tribromide in 40 ml of dichloromethane are slowly added at −70° C. to 13 g of 3-(4-methoxybenzoyl)isoxazole in 200 ml of dichloromethane and stirring is then carried out at room temperature for 3 days. Then, at 0° C., 50 ml of methanol are added dropwise thereto; concentration is carried out and the residue is stirred with 100 ml of 1N hydrochloric acid and 300 ml of ethyl acetate. After concentration of the organic phase and purification over silica gel, 3-(4-hydroxybenzoyl)isoxazole is obtained in the form of beige crystals, m.p: 125-127° C.

Workup

  1. concentrationconcentration
  2. stirringthe residue is stirred with 100 ml of 1N hydrochloric acid and 300 ml of ethyl acetate
  3. customAfter concentration of the organic phase and purification over silica gel

Sources & evidence

ORD record
ord-51c8731b0f664b859d3221c516286ee7
Source dataset
uspto-grants-2009_08
Patent number
US07569727B2

Reaction notes

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