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

HRID 470013ノート

反応式

HRID 470013 の反応式
[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]

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 97324-Fluorophenol

生成物 1

HCID 105351102-Tert-butyl-4-fluorophenol収率 42%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-702c3266a52c42dd818016f260c5ac74
出典データセット
uspto-grants-2014_01
特許番号
US08629162B2

反応ノート

読み込み中…