Hydrochloric Acid → 5-Bromo-2-methylbenzaldehyde

HRID 1625773Notes

Reaction equation

HRID 1625773 reaction equation
CON(C)[C:4](=[O:13])[C:5]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:6]=1[CH3:12].[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1>[Br:11][C:9]1[CH:8]=[CH:7][C:6]([CH3:12])=[C:5]([CH:10]=1)[CH:4]=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 653071935-bromo-N-methoxy-N,2-dimethylbenzamide

Product 1

HCID 104202895-Bromo-2-methylbenzaldehydeYield 92.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the above N-methoxy-N-methyl-5-bromo-2-methylbenzamide (12.2 g) in tetrahydrofuran (100 ml) was cooled to −78° C. under argon atmosphere. To the mixture was added dropwise diisobutyl aluminum hydride (1.0 M toluene solution, 75 ml), and the mixture was stirred at the same temperature for one hour. 10% aqueous hydrochloric acid solution (50 ml) was added thereto, and the mixture was warmed to room temperature. The mixture was extracted with ethyl acetate twice, and washed successively with a saturated aqueous sodium hydrogen carbonate solution and brine. The extract was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was solidified to give 5-bromo-2-methylbenzaldehyde (8.73 g). APCI-Mass m/Z 213/215 (M+H+MeOH−H2O).

Workup

  1. extractionThe mixture was extracted with ethyl acetate twice
  2. washwashed successively with a saturated aqueous sodium hydrogen carbonate solution and brine
  3. dry with materialThe extract was dried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-679f9ea7cdb14178a6642f459d0543b5
Source dataset
uspto-grants-2014_07
Patent number
US08785403B2

Reaction notes

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