Thionyl Chloride → 5-(Chloromethyl)-2,2-difluorobenzo[d][1,3]dioxole

HRID 39126ノート

反応式

HRID 39126 の反応式
S(Cl)([Cl:3])=O.[F:5][C:6]1([F:17])[O:10][C:9]2[CH:11]=[CH:12][C:13]([CH2:15]O)=[CH:14][C:8]=2[O:7]1>ClCCl>[Cl:3][CH2:15][C:13]1[CH:12]=[CH:11][C:9]2[O:10][C:6]([F:17])([F:5])[O:7][C:8]=2[CH:14]=1

参加物

4

反応物 2

HCID 24386Thionyl ChlorideHCID 12814281(2,2-Difluoro-1,3-dioxaindan-5-yl)methanol

生成物 1

HCID 219928095-(Chloromethyl)-2,2-difluorobenzo[d][1,3]dioxole収率 56.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Thionyl chloride (45 g, 38 mmol) was slowly added to a solution of (2,2-difluoro-benzo[1,3]dioxol-5-yl)-methanol (7.2 g, 38 mmol) in dichloromethane (200 mL) at 0° C. The resulting mixture was stirred overnight at room temperature and then evaporated to dryness. The residue was partitioned between an aqueous solution of saturated sodium bicarbonate (100 mL) and dichloromethane (100 mL). The separated aqueous layer was extracted with dichloromethane (150 mL) and the organic layer was dried over sodium sulfate, filtrated, and evaporated to dryness to give crude 5-chloromethyl-2,2-difluoro-benzo[1,3]dioxole (4.4 g) which was used directly in the next step.

後処理

  1. customevaporated to dryness
  2. customThe residue was partitioned between an aqueous solution of saturated sodium bicarbonate (100 mL) and dichloromethane (100 mL)
  3. extractionThe separated aqueous layer was extracted with dichloromethane (150 mL)
  4. dry with materialthe organic layer was dried over sodium sulfate
  5. filtrationfiltrated
  6. customevaporated to dryness

出典と根拠

ORDレコード
ord-58f72746d4f5432c9f853a3f9d16c83c
出典データセット
uspto-grants-2013_09
特許番号
US08524767B2

反応ノート

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