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

HRID 470013노트

반응식

HRID 470013 반응식
[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]

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 97324-Fluorophenol

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-702c3266a52c42dd818016f260c5ac74
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629162B2

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