1-Butanol → 2-Tert-butyl-4-fluorophenol

HRID 1947564Notes

Reaction equation

HRID 1947564 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(O)[CH2:10][CH2:11][CH3:12].S(=O)(=O)(O)O.[CH2:19](Cl)Cl>>[C:11]([C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[OH:8])([CH3:10])([CH3:12])[CH3:19]

Participants

5

Reactant 4

HCID 2631-ButanolHCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 97324-Fluorophenol

Product 1

HCID 105351102-Tert-butyl-4-fluorophenolYield 42%

Procedure

4-Fluorophenol (5 g, 45 mmol) and tent-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-ccf394a702e142f28a3845d85787835c
Source dataset
uspto-grants-2013_03
Patent number
US08399479B2

Reaction notes

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