Ethanol → 4-Fluorocatechol

HRID 2226095Notes

Reaction equation

HRID 2226095 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:8]=1[O:14]C.C(O)C>C(Cl)Cl>[OH:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:8]=1[OH:14]

Participants

5

Reactant 3

HCID 702EthanolHCID 25134Boron tribromideHCID 5936404-Fluoro-1,2-dimethoxybenzene

Product 1

HCID 1604584-FluorocatecholYield 104.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 1 M solution of boron tribromide in methylene chloride (500 mL, 0.50 mole) was cooled to -78 ° C. To this solution was added in a dropwise manner a solution of 46 g (0.30 mole) of 1,2-dimethoxy-4-fluorobenzene in 100 mL of methylene chloride. Upon completion of addition, the mixture was allowed to warm to ambient temperature at which it stirred for about 16 hours. At the conclusion of this period the reaction mixture was cooled to 0° C., and ethanol was added to the reaction mixture. The solvents were evaporated under reduced pressure, leaving 40 g of 1,2-dihydroxy-4-fluorobenzene as a residue. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition
  2. temperatureAt the conclusion of this period the reaction mixture was cooled to 0° C.
  3. customThe solvents were evaporated under reduced pressure

Sources & evidence

ORD record
ord-c5d91d7d367342f6bd1ab91b35583ba7
Source dataset
uspto-grants-1994_09
Patent number
US05346881

Reaction notes

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