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

HRID 73975Notes

Reaction equation

HRID 73975 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>C(Cl)Cl>[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 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Fluorophenol (5 g, 45 mmol) and tert-butanol (5.9 mL, 63 mmol) were dissolved in CH2Cl2 (80 mL) and treated with concentrated sulfuric acid (98%, 3 mL). The mixture was stirred at room temperature overnight. The organic layer was washed with water, neutralized with NaHCO3, dried over MgSO4 and concentrated. The residue was purified by column chromatography (5-15% EtOAc-Hexane) to give 2-tert-butyl-4-fluorophenol (3.12 g, 42%). 1H NMR (400 MHz, DMSO-d6) δ 9.32 (s, 1H), 6.89 (dd, J=11.1, 3.1 Hz, 1H), 6.84-6.79 (m, 1H), 6.74 (dd, J=8.7, 5.3 Hz, 1H), 1.33 (s, 9H).

Workup

  1. washThe organic layer was washed with water
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography (5-15% EtOAc-Hexane)

Sources & evidence

ORD record
ord-b88e3f2a5ea14c04a16d70d9a82182ab
Source dataset
uspto-grants-2014_09
Patent number
US08829204B2

Reaction notes

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