Thionyl Chloride → HCID 69215076, compound

HRID 2221525Notes

Reaction equation

HRID 2221525 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:21]O)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[N:11]=[C:12]([C:16]2[O:17][CH:18]=[CH:19][CH:20]=2)[O:13][C:14]=1[CH3:15].S(Cl)([Cl:25])=O>>[Br:1][C:2]1[CH:3]=[C:4]([CH2:21][Cl:25])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[N:11]=[C:12]([C:16]2[O:17][CH:18]=[CH:19][CH:20]=2)[O:13][C:14]=1[CH3:15]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 23076558HCID 23076558, compound

Product 1

HCID 69215076HCID 69215076, compoundYield 87%

Procedure

(3-bromo-4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}phenyl)methanol (4.20 g) was added to thionyl chloride (5 mL) at 0° C., and the mixture was stirred for 2 hrs. The reaction mixture was concentrated, saturated aqueous sodium hydrogen carbonate was added to the residue and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate and concentrated to give 4-{[2-bromo-4-(chloromethyl)phenoxy]methyl}-2-(2-furyl)-5-methyloxazole as pale-yellow crystals (3.82 g, yield 87%). Recrystallization from ethyl acetate-hexane gave pale-yellow needle crystals. melting point: 125-126° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionsaturated aqueous sodium hydrogen carbonate was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cea8e6cf5736442f8aaaf8f51368ba4d
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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