Hydrochloric Acid → (3-Bromo-2,6-difluorophenyl)methanol

HRID 1794133Notes

Reaction equation

HRID 1794133 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([CH2:9]Br)[C:3]=1[F:11].O.C(=O)([O-])[O-:14].[Ca+2].Cl>O1CCOCC1>[Br:1][C:2]1[C:3]([F:11])=[C:4]([CH2:9][OH:14])[C:5]([F:8])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 10112Calcium CarbonateHCID 222200841-Bromo-3-(bromomethyl)-2,4-difluorobenzene

Product 1

HCID 22219889(3-Bromo-2,6-difluorophenyl)methanolYield 114.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1-Bromo-3-(bromomethyl)-2,4-difluoro-benzene (45.2 g, 0.158 M) was dissolved in dioxane (800 mL), water (800 mL) and calcium carbonate (80 g, 0.80 M) were added and the mixture was refluxed for 16 h. The mixture was cooled, acidified with 2N HCl and extracted with dichloromethane. Organic phases were pooled, dried with Na2SO4 and and evaporated to yield a brownish oil (40.3 g). The residue was purified by column chromatography (silica gel; n-hexane/ethyl acetate 9:1) to yield 31.2 g (88%) of the title compound as a colorless solid. MS (EI): 224.0 (M)+.

Workup

  1. temperaturethe mixture was refluxed for 16 h
  2. temperatureThe mixture was cooled
  3. extractionextracted with dichloromethane
  4. dry with materialdried with Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-1b78b2f41c6f46f9bbcab581642754b2
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

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