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

HRID 1010553Notes

Reaction equation

HRID 1010553 reaction equation
[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

Participants

3

Reactant 2

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

Product 1

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

Procedure

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.

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

Sources & evidence

ORD record
ord-07821d18a4204c35b65c9292c2661502
Source dataset
uspto-grants-2011_07
Patent number
US07977322B2

Reaction notes

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