Methanol → HCID 67799948, compound

HRID 275263Notes

Reaction equation

HRID 275263 reaction equation
P(Br)(Br)[Br:2].[F:5][C:6]1[C:13]([F:14])=[C:12]2[CH:15]=[CH:16][C:7]=1[CH:8](O)[O:9][CH2:10][O:11]2.CO.O>C(OCC)C>[F:5][C:6]1[C:13]([F:14])=[C:12]2[CH:15]=[CH:16][C:7]=1[CH:8]([Br:2])[O:9][CH2:10][O:11]2

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 24614Phosphorus tribromideHCID 67799769HCID 67799769, compound

Product 1

HCID 67799948HCID 67799948, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Phosphorus tribromide (47 g) was added to a solution of 2,3difluoromethylenedioxybenzyl alcohol (32 g) in diethyl ether at 0° C. After 0.5 hours the reaction mixture was allowed to warm to ambient temperature and was stirred at ambient temperature for 3 hours. The reaction mixture was then cooled to 0° C., methanol was added followed by water, the mixture was extracted with diethyl ether, separated and the organic layer washed with saturated sodium bicarbonate (until neutral), dried and the solvent removed to yield the product as a pale yellow oil, (40.4 g), NMR (CDCl3): 4.50(s,2H), 7.10(m,3H).

Workup

  1. temperatureThe reaction mixture was then cooled to 0° C.
  2. extractionthe mixture was extracted with diethyl ether
  3. customseparated
  4. washthe organic layer washed with saturated sodium bicarbonate (until neutral)
  5. customdried
  6. customthe solvent removed

Sources & evidence

ORD record
ord-8c34b5288764407cb5ce62cc4dff3986
Source dataset
uspto-grants-1995_02
Patent number
US05393730

Reaction notes

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