Sulfuric Acid → 2-Tert-butyl-4-fluorophenol

HRID 2041960Notes

Reaction equation

HRID 2041960 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[C:9](O)([CH3:12])([CH3:11])[CH3:10].S(=O)(=O)(O)O>ClCCl>[C:9]([C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[OH:8])([CH3:12])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 97324-Fluorophenol

Product 1

HCID 105351102-Tert-butyl-4-fluorophenolYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-fluorophenol (5.00 g, 45.0 mmol) and tert-butanol (4.67 g, 63.0 mmol) in dichloromethane (80 mL) was added conc. sulfuric acid (3.0 mL) at room temperature. After 16 h the reaction mixture was concentrated under reduced pressure and the resulting residue was diluted with ethyl acetate. The organic layer was washed with water, neutralized with saturated sodium hydrogen carbonate, dried (Na2SO4), filtered and concentrated under reduced pressure. Purification by flash column chromatography (silica gel, 100:0 to 90:10 heptane/ethyl acetate) provided 2-tert-butyl-4-fluorophenol (2.54 g, 34%) as a pale green oil.

Workup

  1. concentrationAfter 16 h the reaction mixture was concentrated under reduced pressure
  2. additionthe resulting residue was diluted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash column chromatography (silica gel, 100:0 to 90:10 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-d539467ef2a04ef09ab7d9e2ac1d936c
Source dataset
uspto-grants-2013_11
Patent number
US08586571B2

Reaction notes

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