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

HRID 529995Notes

Reaction equation

HRID 529995 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.S(Cl)([Cl:16])=O>>[Cl:16][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 24386Thionyl ChlorideHCID 12814281(2,2-Difluoro-1,3-dioxaindan-5-yl)methanol

Product 1

HCID 219928095-(Chloromethyl)-2,2-difluorobenzo[d][1,3]dioxoleYield 89%

Procedure

A solution of (2,2-difluorobenzo[d][1,3]dioxol-5-yl)methanol (120 g, 0.64 mol) in neat thionyl chloride (500 mL) was stirred for 2 h at 25° C. The excess thionyl chloride was distilled off in vacuo. The residue was partitioned between saturated NaHCO3 (400 mL) and dichloromethane (200 mL). The separated aqueous layer was extracted with dichloromethane (300 mL×3). The combined organic layers were dried, filtered and concentrated in vacuo to give 5-(chloromethyl)-2,2-difluorobenzo[d][1,3]dioxol (117.6 g, 89%), which was directly used in the next step.

Workup

  1. distillationThe excess thionyl chloride was distilled off in vacuo
  2. customThe residue was partitioned between saturated NaHCO3 (400 mL) and dichloromethane (200 mL)
  3. extractionThe separated aqueous layer was extracted with dichloromethane (300 mL×3)
  4. customThe combined organic layers were dried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cb25c5cf122545eeb6532987f4168301
Source dataset
uspto-grants-2016_05
Patent number
US09351962B2

Reaction notes

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