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

HRID 1909588Notes

Reaction equation

HRID 1909588 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-6d1ab824835b40cebe04787b4b1a266a
Source dataset
uspto-grants-2013_12
Patent number
US08598374B2

Reaction notes

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