Thionyl Chloride → 7-(Chloromethyl)-5,6-difluoro-2,2-dimethyl-2,3-dihydrobenzofuran

HRID 445873Notes

Reaction equation

HRID 445873 reaction equation
[F:1][C:2]1[C:3]([F:15])=[C:4]([CH2:13]O)[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[CH2:7][C:6]=2[CH:12]=1.O=S(Cl)[Cl:18]>ClCCl>[Cl:18][CH2:13][C:4]1[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[CH2:7][C:6]=2[CH:12]=[C:2]([F:1])[C:3]=1[F:15]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 58566591(5,6-difluoro-2,2-dimethyl-3H-benzofuran-7-yl)methanol

Product 1

HCID 585665727-(Chloromethyl)-5,6-difluoro-2,2-dimethyl-2,3-dihydrobenzofuranYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (5,6-difluoro-2,2-dimethyl-3H-benzofuran-7-yl)methanol (736) (0.18 g, 0.84 mmol) in anhydrous dichloromethane (5 mL) was added SOCl2 dropwise at 0° C. The mixture was stirred at room temperature for 2 h. The solvent was removed in vacuo, and the residue was dissolved in EtOAc (100 mL). The solution was washed with water (30 mL), dried over anhydrous sodium sulfate, and evaporated in vacuo to give a solid 7-(chloromethyl)-5,6-difluoro-2,2-dimethyl-2,3-dihydrobenzofuran (737) (0.194 g, 99%).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in EtOAc (100 mL)
  3. washThe solution was washed with water (30 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-e4c74c3f1fc44889a73374d8aea83dbf
Source dataset
uspto-grants-2013_07
Patent number
US08476308B2

Reaction notes

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