Thionyl Chloride → 5-Bromo-7-(chloromethyl)-2,2-dimethyl-2,3-dihydrobenzofuran

HRID 1876403Notes

Reaction equation

HRID 1876403 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:13]O)[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[CH2:7][C:6]=2[CH:12]=1.S(Cl)([Cl:17])=O>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH2:13][Cl:17])[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[CH2:7][C:6]=2[CH:12]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 58566787(5-Bromo-2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)methanol

Product 1

HCID 585664675-Bromo-7-(chloromethyl)-2,2-dimethyl-2,3-dihydrobenzofuran

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (5-bromo-2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)methanol (669) (390 mg, 1.51 mmol) in dichloromethane (15 mL) was added thionyl chloride (0.56 mL, 7.58 mmol). The reaction was stirred at room temperature for 2 hours and then concentrated to afford 5-bromo-7-(chloromethyl)-2,2-dimethyl-2,3-dihydrobenzofuran (670).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-77efed5feabb4e14938e28373370a258
Source dataset
uspto-grants-2012_11
Patent number
US08309600B2

Reaction notes

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