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

HRID 2043224Notes

Reaction equation

HRID 2043224 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]dioxole (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-c17776c41ec54af39b75cf113103e4f3
Source dataset
uspto-grants-2013_11
Patent number
US08586615B2

Reaction notes

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