Triethylamine → 7-(Chloromethyl)-5-fluoro-2,3-dihydro-1,4-benzodioxine

HRID 253303노트

반응식

HRID 253303 반응식
[F:1][C:2]1[C:7]2[O:8][CH2:9][CH2:10][O:11][C:6]=2[CH:5]=[C:4]([CH2:12]O)[CH:3]=1.C(N(CC)CC)C.S(Cl)([Cl:23])=O>ClCCl>[Cl:23][CH2:12][C:4]1[CH:3]=[C:2]([F:1])[C:7]2[O:8][CH2:9][CH2:10][O:11][C:6]=2[CH:5]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 66891073(8-Fluoro-2,3-dihydro-1,4-benzodioxin-6-yl)methanol

생성물 1

HCID 668893987-(Chloromethyl)-5-fluoro-2,3-dihydro-1,4-benzodioxine수율 99.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

To a solution of (8-fluoro-2,3-dihydro-1,4-benzodioxin-6-yl)methanol (0.84 g, 4.55 mmol) and triethylamine (960 μl, 4.84 mmol) in dichloromethane (20 mL) was slowly added thionyl chloride (400 μl, 5.47 mmol) at 0° C. The solution was stirred at 0° C. for 15 min then at rt for 3 h. Dichloromethane (80 mL) was added and the solution was washed with water (40 mL), saturated aqueous sodium bicarbonate (40 mL) then brine (40 mL) and dried over sodium sulfate. Filtration and concentration gave 7-(chloromethyl)-5-fluoro-2,3-dihydro-1,4-benzodioxine (0.92 g, quantitative yield) as a brown oil. The chloride was used in the next step without further purification.

후처리

  1. customat 0° C
  2. waitat rt for 3 h
  3. washthe solution was washed with water (40 mL), saturated aqueous sodium bicarbonate (40 mL)
  4. dry with materialbrine (40 mL) and dried over sodium sulfate
  5. filtrationFiltration and concentration

출처 및 근거

ORD 기록
ord-a09af8cc166b4f4b96e94c5d17242f8f
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07872014B2

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