Hydrochloric Acid → 1-Bromo-2-(chloromethyl)-4,5-dimethoxybenzene

Reaction equation

[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[CH2:12]O.[ClH:14]>>[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[CH2:12][Cl:14]

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 618887(2-Bromo-4,5-dimethoxyphenyl)methanol

Product 1

HCID 49622811-Bromo-2-(chloromethyl)-4,5-dimethoxybenzene

Procedure

(2-Bromo-4,5-dimethoxy-phenyl)-methanol (25.09 g, 0.1015 mol) was added as a solid to a vigorously stirred solution of concentrated aqueous HCl (75 mL). The resulting white suspension was stirred at room temperature for 30 min. The resulting mixture was then extracted with CH2Cl2 (3×) and the combined extracts dried over MgSO4, filtered and concentrated in vacuo to yield 1-bromo-2-chloromethyl-4,5-dimethoxy-benzene as a white solid.

Workup

extractionThe resulting mixture was then extracted with CH2Cl2 (3×)
dry with materialthe combined extracts dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-0503ddf4208249beafe3494827e48c26
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673890B2

Reaction notes

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