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

HRID 253303ノート

反応式

HRID 253303 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a09af8cc166b4f4b96e94c5d17242f8f
出典データセット
uspto-grants-2011_01
特許番号
US07872014B2

反応ノート

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