Trimethyl orthoformate → 1-Bromo-4-(dimethoxymethyl)benzene

HRID 380224Notes

Reaction equation

HRID 380224 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5](C=O)=[CH:4][CH:3]=1.[CH:10](OC)([O:13][CH3:14])[O:11][CH3:12].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C[O-].[Na+]>CO>[CH3:12][O:11][CH:10]([O:13][CH3:14])[C:5]1[CH:8]=[CH:9][C:2]([Br:1])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 9005Trimethyl orthoformateHCID 707414-BromobenzaldehydeHCID 521998p-Toluenesulfonic acid monohydrateHCID 10942334Sodium Methoxide

Product 1

HCID 6883421-Bromo-4-(dimethoxymethyl)benzene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

21.1 g (114 mmol) of 4-bromobenzaldehyde and 20 ml (182 mmol) of trimethyl orthoformate (both Fluka, Buchs, Switzerland) are dissolved in 35 ml of methanol, and 0.65 g (3.4 mmol) of p-toluenesulfonic acid monohydrate is added at room temperature (exothermic reaction). The reaction mixture is stirred at room temperature under nitrogen for 20 hours. The acid is then neutralised with 0.62 ml of 30% sodium methanolate solution in methanol (3.4 mmol); the reaction mixture is concentrated using a rotary evaporator and the residue is distilled. The title compound is obtained in the form of a colourless liquid. TLC: Rf=0.58 (hexane/ethyl acetate 2:1). B.p.: 90-92° C. (4 mbar). 1H-NMR (CDCl3; 200 MHz): 7.50 and 7.32/each d, J=9 (2×2H); 5.36/s (1H); 3.31/s (6H).

Workup

  1. custom(exothermic reaction)
  2. concentrationthe reaction mixture is concentrated
  3. customa rotary evaporator
  4. distillationthe residue is distilled

Sources & evidence

ORD record
ord-e2989b6615fc46b98d02ee850918d80b
Source dataset
uspto-grants-2001_10
Patent number
US06300519B1

Reaction notes

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