Ethyl orthoformate → 5-Bromo-1-diethoxymethyl-2-methoxy-3-trifluoromethoxybenzene

HRID 385142Notes

Reaction equation

HRID 385142 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:12][C:13]([F:16])([F:15])[F:14])[C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)C=O.[CH:17]([O:24][CH2:25][CH3:26])([O:21][CH2:22][CH3:23])OCC>CCCCCC>[Br:1][C:2]1[CH:3]=[C:4]([O:12][C:13]([F:14])([F:15])[F:16])[C:5]([O:10][CH3:11])=[C:6]([CH:17]([O:21][CH2:22][CH3:23])[O:24][CH2:25][CH3:26])[CH:9]=1

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 866681815-Bromo-2-methoxy-3-(trifluoromethoxy)benzaldehyde

Product 1

HCID 681086775-Bromo-1-diethoxymethyl-2-methoxy-3-trifluoromethoxybenzene

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

5-bromo-2-methoxy-3-trifluoromethoxybenzaldehyde (5.22 g) was dissolved in n-hexane (15 mL) and triethyl orthoformate (4.4 mL), and Amberlyst-15 (522 mg) was added to the solution, and then the mixture was refluxed for 3 hours. The reaction solution was filtered, and then the solvent was distilled off under reduced pressure to obtain the title compound (6.19 g) as a brown oily substance.

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. filtrationThe reaction solution was filtered
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-a9f2bd6d3f5c4c60a296d297a85a4611
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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