Ethyl orthoformate → HCID 15114404, compound

HRID 501717

Reaction equation

HRID 501717 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:7](C(F)(F)F)=[CH:6][C:3]=1C=O.[OH2:14].[C:15]1(C)C=CC(S(O)(=O)=O)=CC=1.C(O[CH:29]([O:33][CH2:34]C)[O:30][CH2:31]C)C>CO>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([O:14][CH3:15])=[CH:6][C:3]=1[CH:29]([O:30][CH3:31])[O:33][CH3:34]

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 521998p-Toluenesulfonic acid monohydrateHCID 70180472-Bromo-5-(trifluoromethyl)benzaldehyde

Product 1

HCID 15114404HCID 15114404, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Step AJ (1): 2-Bromo-5-(trifluoromethyl)benzaldehyde (1069 mg, 4.975 mmol) was dissolved in a mixture of methanol (20 mL) and triethylorthoformate (20 mL). p-Toluenesulfonic acid monohydrate (180.0 mg, 0.946 mmol) was added and the reaction mixture was stirred under reflux for 5 h. The reaction was quenched with aqueous NaHCO3 and extracted with DCM. The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuum at the temperature, not exceeding 35° C. The residue was purified by silica gel chromatography to give 1-bromo-2-(dimethoxymethyl)-4-methoxybenzene (1060 mg, 71%) as a colorless oil. LC-MS (M−OCH3)+=267.23.

Workup

  1. temperatureunder reflux for 5 h
  2. customThe reaction was quenched with aqueous NaHCO3
  3. extractionextracted with DCM
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum at the temperature
  7. customexceeding 35° C
  8. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-25ca6c9a1559491c99e95eb8418e6fef
Source dataset
uspto-grants-2010_08
Patent number
US07772221B2

Linked notes

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