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

HRID 401310노트

반응식

HRID 401310 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-3b4af6a20c024d7cb02da6f46efbe6a2
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741925B2

반응 노트

불러오는 중…