Triethylamine → 1-Bromo-5-(dimethoxymethyl)-4-fluoro-2-methoxybenzene

HRID 602379Notes

Reaction equation

HRID 602379 reaction equation
[Br:1][C:2]1[C:3]([O:11][CH3:12])=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)C=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH:25]([O:30][CH3:31])([O:28][CH3:29])OC.C(N(CC)CC)C>CO.[Cl-].[Na+].O.C(OCC)(=O)C>[CH3:31][O:30][CH:25]([O:28][CH3:29])[C:6]1[CH:9]=[C:2]([Br:1])[C:3]([O:11][CH3:12])=[CH:4][C:5]=1[F:10]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 9005Trimethyl orthoformateHCID 521998p-Toluenesulfonic acid monohydrateHCID 121872105-Bromo-2-fluoro-4-methoxybenzaldehyde

Product 1

HCID 670613071-Bromo-5-(dimethoxymethyl)-4-fluoro-2-methoxybenzeneYield 100%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

5-Bromo-2-fluoro-4-methoxybenzaldehyde (1 g, 4.3 mmol), p-toluenesulfonic acid monohydrate (163 mg, 0.86 mmol) and trimethyl orthoformate (2.4 mL, 21 mmol) were dissolved in methanol (20 mL) and stirred under heating and reflux for 1 hour. After standing to cool the reaction mixture, triethylamine (2 mL) was added thereto and further stirred for 10 minutes. The mixture was added with saturated brine and ethyl acetate, and the organic layer was separated, followed by washing with saturated brine. The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure to obtain 5-bromo-2-fluoro-4-methoxybenzaldehyde dimethylacetal (1.19 g, 100%).

Workup

  1. temperatureunder heating
  2. temperaturereflux for 1 hour
  3. additionwas added
  4. stirringfurther stirred for 10 minutes
  5. customthe organic layer was separated
  6. washby washing with saturated brine
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-07cd30235450420b9174ade536a6948d
Source dataset
uspto-grants-2011_03
Patent number
US07906522B2

Reaction notes

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