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

HRID 45277

Reaktionsgleichung

Reaktionsgleichung von HRID 45277
[F:1][C:2]1([F:13])[O:6][C:5]2[CH:7]=[CH:8][C:9]([CH2:11]O)=[CH:10][C:4]=2[O:3]1.[Cl:14]CCl>>[Cl:14][CH2:11][C:9]1[CH:8]=[CH:7][C:5]2[O:6][C:2]([F:13])([F:1])[O:3][C:4]=2[CH:10]=1

Komponenten

3

Edukt 2

HCID 6344DichloromethaneHCID 12814281(2,2-Difluoro-1,3-dioxaindan-5-yl)methanol

Produkt 1

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

Versuchsvorschrift

5-Chloromethyl-2,2-difluoro-benzo[1,3]dioxole 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 combined organic layers were 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.

Aufarbeitung

  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 combined organic layers were dried over sodium sulfate
  5. filtrationfiltrated
  6. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-3b28cf3b4c244bee8114ff46f1491175
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541453B2

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