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

HRID 39444

Reaktionsgleichung

Reaktionsgleichung von HRID 39444
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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 219928095-(Chloromethyl)-2,2-difluorobenzo[d][1,3]dioxoleAusbeute 56,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

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 organic layer was dried over sodium sulfate
  5. filtrationfiltrated
  6. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-b9ba30b91d534951b0c4653ca6b76159
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524910B2

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