Catechol → 4-Fluoro-2H-1,3-benzodioxole

HRID 495024

反応式

HRID 495024 の反応式
BrCBr.[F:4][C:5]1[CH:11]=[CH:10][CH:9]=[C:7]([OH:8])[C:6]=1[OH:12].[C:13]1(C(=CC=CC=1)O)O>[Cl-].C[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC.[OH-].[Na+].C(Cl)Cl.O>[F:4][C:5]1[CH:11]=[CH:10][CH:9]=[C:7]2[O:8][CH2:13][O:12][C:6]=12

参加物

8

反応物 3

HCID 289CatecholHCID 3024DibromomethaneHCID 677643-Fluorocatechol

生成物 1

HCID 157672604-Fluoro-2H-1,3-benzodioxole

試薬・触媒・溶媒 4

HCID 21218Trioctylmethylammonium chloride触媒HCID 962Water溶媒2 回HCID 6344Dichloromethane溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

Alliquat 336 (methyltrioctylammonium chloride (0.63 g, 0.0016 mol), dibromomethane (40.7 g, 234.2 mmol), and water (31 mL) were placed in a 500 mL 3-necked flask equipped with an addition funnel, condenser and a stir bar. The addition funnel was charged with a solution of 3-fluorocatechol (20.0 g, 6.1 mmol) in 5M sodium hydroxide (80 mL). The mixture in the flask was heated to reflux and the solution of the catechol was added dropwise with good stirring over 1.5 hours. The resulting dark mixture was heated an additional 2 hours at reflux. After cooling to room temperature, the reaction was diluted with methylene chloride and water. The aqueous layer was extracted with methylene chloride and the combined organic layers were dried and concentrated to give 1-fluoro-2,3-methylenedioxybenzene (14.6 g, 104.2 mmol) as a dark yellow oil: 1H NMR (CDCl3): δ 6.80 (m, 1H), 6.68 (m, 2H), 6.04 (s, 2H).

後処理

  1. customequipped with an addition funnel, condenser and a stir bar
  2. temperatureThe mixture in the flask was heated
  3. temperatureto reflux
  4. temperatureThe resulting dark mixture was heated an additional 2 hours
  5. temperatureat reflux
  6. extractionThe aqueous layer was extracted with methylene chloride
  7. customthe combined organic layers were dried
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-3eb7de94d4b447aca1624806392c413c
出典データセット
uspto-grants-2009_05
特許番号
US07538214B2

関連ノート

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