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

HRID 1876431Notes

Reaction equation

HRID 1876431 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-1e2ddd3b929a45fe8369cc6d87c49c87
Source dataset
uspto-grants-2012_11
Patent number
US08309600B2

Reaction notes

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