Trimethyl orthoformate → 1-Bromo-2-(dimethoxymethyl)benzene

HRID 483284Notes

Reaction equation

HRID 483284 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1C=O.[CH:10](OC)([O:13][CH3:14])[O:11][CH3:12]>CO.Cl>[CH3:12][O:11][CH:10]([O:13][CH3:14])[C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[Br:1]

Participants

5

Reactant 2

HCID 9005Trimethyl orthoformateHCID 811292-Bromobenzaldehyde

Product 1

HCID 111489431-Bromo-2-(dimethoxymethyl)benzeneYield 84.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-bromobenzaldehyde (451.9 g, 2.44 mol), trimethyl orthoformate (324 g, 3.05 mol) and concentrated hydrochloric acid (4.0 ml, 0.05 mol) in methanol (2 L) was refluxed for four hours. The volatile components were evaporated on the rotary evaporator and the residue dried over anhydrous potassium carbonate, filtered, and distilled (66°-72° C. at 0.1-0.2 mm) to give 474.1 g (84%) of the 2-Bromobenzaldehyde Dimethyl Acetal compound as a colorless oil. 'H NMR (CDCl3): 3.35 (s, 6, OCH3), 5.50 (s, 1, CH), 7.5 (m, 4, Ar--H).

Workup

  1. customThe volatile components were evaporated on the rotary evaporator
  2. dry with materialthe residue dried over anhydrous potassium carbonate
  3. filtrationfiltered
  4. distillationdistilled (66°-72° C. at 0.1-0.2 mm)

Sources & evidence

ORD record
ord-7f55b50b0f85443aa550f46be2151bee
Source dataset
uspto-grants-1986_03
Patent number
US04578522

Reaction notes

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