Methanol → HCID 14971865, compound

HRID 1656420Notes

Reaction equation

HRID 1656420 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]([NH2:16])=[O:15])[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br.CO>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]([C:9]2[O:13][CH:12]=[N:11][C:10]=2[C:14]([NH2:16])=[O:15])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 14971864HCID 14971864, compound

Product 1

HCID 14971865HCID 14971865, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

5-(3-Methoxyphenyl)-4-oxazolecarboxamide (1.29 g, 5.9 mmol) was dissolved in dichloromethane (120 mL) and cooled to about 0° C. under N2. Boron tribromide solution (29 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 10 min the solution was concentrated onto SiO2 and chromatographed (elution with 20% methanol/ethyl acetate) to give the phenol 848 mg (70%), mp 202°-204° C.IR (KBr, cm-1) 3398, 3188, 3132, 1684, 1608, 1572, 1254, 1190, 866, 694, 618. 1H NMR (300 MHz, DMSO-d6)δ 6.82 to 6.85 (1H, m), 7.26 (1H, t, J=8.0 Hz) 7.56 to 7.69 (4H, m), 8.49 (1H, s), 9.66 (1H, s). 13C NMR 75 MHz, DMSO-d6) ppm 114.62, 116.95, 118.59, 128.08, 129.04, 129.52, 149.87, 151.10, 157.22, 162.80. m/e 205 (MH+).

Workup

  1. customreacts vigorously}
  2. stirringafter being stirred 10 min the solution
  3. concentrationwas concentrated onto SiO2
  4. customchromatographed
  5. wash(elution with 20% methanol/ethyl acetate)

Sources & evidence

ORD record
ord-bb0970fd7b0b4060af8716414e4609d6
Source dataset
uspto-grants-1993_10
Patent number
US05254576

Reaction notes

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