Methanol → HCID 14971872, compound

HRID 1656419Notes

Reaction equation

HRID 1656419 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:9]2[O:13][CH:12]=[N:11][C:10]=2[C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:15]=2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br.CO>ClCCl>[C:19]1([C:16]2[C:15]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[C:14]([C:10]3[N:11]=[CH:12][O:13][C:9]=3[C:5]3[CH:4]=[C:3]([OH:2])[CH:8]=[CH:7][CH:6]=3)[O:18][N:17]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 14971871HCID 14971871, compound

Product 1

HCID 14971872HCID 14971872, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

5-[5-(3-Methoxyphenyl)-4-oxazolyl]-3,4-diphenylisoxazole (25) (1.01 g, 2.56 mmol) was dissolved in dichloromethane (65 mL) and cooled to about 0° C. under N2. Boron tribromide solution (13 mL of 1 M in dichloromethane) was added dropwise and the solution stirred about 18 hours at room temperature. Methanol (10 mL) was added dropwise {caution: reacts vigorously}, and after being stirred about 10 minutes the solution was concentrated on to SiO2 and chromatographed (elution with 10% ethyl acetate/chloroform) to give the phenol 631 mg (68%), mp 199°-200° C.

Workup

  1. customreacts vigorously}
  2. stirringafter being stirred about 10 minutes the solution
  3. concentrationwas concentrated on to SiO2
  4. customchromatographed
  5. wash(elution with 10% ethyl acetate/chloroform)

Sources & evidence

ORD record
ord-dc4463de2dd94c44ba967dde37e2dbe8
Source dataset
uspto-grants-1993_10
Patent number
US05254576

Reaction notes

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