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

HRID 83690Notes

Reaction equation

HRID 83690 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-9420a62f99b547138e19cb6b6f7f4bfc
Source dataset
uspto-grants-2014_09
Patent number
US08846753B2

Reaction notes

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