Water → 5-Fluoronaphthalen-1-ol

HRID 2075547Notes

Reaction equation

HRID 2075547 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[O:12]C.B(Br)(Br)Br.O>ClCCl>[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[OH:12]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromide2×HCID 123363901-Fluoro-5-methoxynaphthalene

Product 1

HCID 123363915-Fluoronaphthalen-1-olYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A stirred solution of 2.08 g of 5-fluoro-1-methoxynaphthalene in 42 ml of dry dichloromethane was cooled to −60 to −65° C. after which was added 13 ml of 1M BBr3 in dichloromethane. The mixture was allowed to warm to room temperature, and stirred at RT for 1 h. The reaction mixture was again cooled to −60 to −65° C. after which was added an additional 13 ml of 1M BBr3 in dichloromethane. The mixture was allowed to warm to RT and stirred at RT for 1.5 h. The mixture was poured into cold water, extracted twice with dichloromethane, dried (sodium sulphate), filtered and concentrated to a purple/white solid. The material was dissolved in a minimum volume of dichloromethane and flash chromatographed on silica gel, eluting with ethyl acetate/dichloromethane/heptane to provide 1.58 g (83%) of 5-fluoro-1-hydroxynaphthalene as a white solid.

Workup

  1. temperatureThe reaction mixture was again cooled to −60 to −65° C. after which
  2. temperatureto warm to RT
  3. stirringstirred at RT for 1.5 h
  4. extractionextracted twice with dichloromethane
  5. dry with materialdried (sodium sulphate)
  6. filtrationfiltered
  7. concentrationconcentrated to a purple/white solid
  8. dissolutionThe material was dissolved in a minimum volume of dichloromethane and flash
  9. customchromatographed on silica gel
  10. washeluting with ethyl acetate/dichloromethane/heptane

Sources & evidence

ORD record
ord-14f9347138da4f2eaaa35365803f9d50
Source dataset
uspto-grants-2011_04
Patent number
US07919628B2

Reaction notes

Loading…