Benzene → HCID 10905438, compound

HRID 233282Notes

Reaction equation

HRID 233282 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24]O)=[CH:18][CH:17]=1.C1C=CC=CC=1.P(Br)(Br)[Br:33]>O>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][Br:33])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 24614Phosphorus tribromideHCID 10925764HCID 10925764, compound

Product 1

HCID 10905438HCID 10905438, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 3-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]propan-1-ol (2.6 g) and benzene (50 ml) was added phosphorus tribromide (PBr3) (2.1 g), which was stirred for 2 hours at 70° C. The reaction mixture was poured into water, which was subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), then the solvent was distilled off to leave 3-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]propyl bromide (0.98 g, 32%), which was recrystallized from ethyl acetate--hexane to give colorless needles, m.p.78°-79° C.

Workup

  1. extractionwas subjected to extraction with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-6d043002c8474be7b5260eebcf27c891
Source dataset
uspto-grants-1997_01
Patent number
US05591862

Reaction notes

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