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

HRID 1964183Notes

Reaction equation

HRID 1964183 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a5ed6d2fec0b4d8a9da4b6238e54f6db
Source dataset
uspto-grants-2013_04
Patent number
US08415387B2

Reaction notes

Loading…