Methanol → HCID 15487823, compound

HRID 636703Notes

Reaction equation

HRID 636703 reaction equation
[C:1]1([C:7]2[O:8][CH:9]=[C:10]([CH2:12][CH2:13][O:14][C:15]3[CH:20]=[CH:19][C:18]([CH2:21]O)=[CH:17][CH:16]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Br)(Br)[Br:24].CO>C(Cl)Cl>[C:1]1([C:7]2[O:8][CH:9]=[C:10]([CH2:12][CH2:13][O:14][C:15]3[CH:20]=[CH:19][C:18]([CH2:21][Br:24])=[CH:17][CH:16]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 24614Phosphorus tribromideHCID 154878222-Phenyl-4-(4-hydroxymethylphenoxy)ethyloxazole

Product 1

HCID 15487823HCID 15487823, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-phenyl-4-(4-hydroxymethylphenoxy)ethyloxazole (30 g, 102 mmol) in 300 mL of methylene chloride at 5° C under a nitrogen atmosphere was added phosphorous tribromide (10.02 mL, 107 mmol) dropwise keeping the temperature of the reaction below 20° C. The resulting solution was allowed to stir for about 2 hours at room temperature. The reaction was cooled to about 10° C and 20 mL of methanol was added. After about 5 minutes, the solvent was removed and the solid remaining was partitioned between 1.35 L of ethyl acetate and 1.05 L of cold 5% aqueous sodium bicarbonate. The organics were washed with another 1.05 L of 5% aqueous sodium bicarbonate, dried over magnesium sulfate, filtered, and removed to give 33.3 g of the title compound.

Workup

  1. customthe temperature of the reaction below 20° C
  2. temperatureThe reaction was cooled to about 10° C
  3. waitAfter about 5 minutes
  4. customthe solvent was removed
  5. customthe solid remaining was partitioned between 1.35 L of ethyl acetate and 1.05 L of cold 5% aqueous sodium bicarbonate
  6. washThe organics were washed with another 1.05 L of 5% aqueous sodium bicarbonate
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customremoved

Sources & evidence

ORD record
ord-04958cd1dc3442a78383efc8ba501211
Source dataset
uspto-grants-2001_02
Patent number
US06194446B1

Reaction notes

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