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

HRID 495024

반응식

HRID 495024 반응식
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

참가 물질

8

반응물 3

HCID 289CatecholHCID 3024DibromomethaneHCID 677643-Fluorocatechol

생성물 1

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

시약·촉매·용매 4

HCID 21218Trioctylmethylammonium chloride촉매HCID 962Water용매2회HCID 6344Dichloromethane용매HCID 14798Sodium Hydroxide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-3eb7de94d4b447aca1624806392c413c
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538214B2

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