Hydrochloric Acid → 3,5-Difluorobenzaldehyde

HRID 2121092Notes

Reaction equation

HRID 2121092 reaction equation
[Mg].[F:2][C:3]1[CH:4]=[C:5](Br)[CH:6]=[C:7]([F:9])[CH:8]=1.CN(C)[CH:13]=[O:14].Cl>O1CCCC1>[F:2][C:3]1[CH:4]=[C:5]([CH:6]=[C:7]([F:9])[CH:8]=1)[CH:13]=[O:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 1363131-Bromo-3,5-difluorobenzeneHCID 5462224Magnesium

Product 1

HCID 5881603,5-DifluorobenzaldehydeYield 84.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 28 g portion of magnesium turnings was suspended in 60 ml of tetrahydrofuran (THF) to which was subsequently added dropwise 800 ml of THF solution containing 200 g of 3,5-difluoro-1-bromobenzene at such a rate that the solvent was gently refluxed. After the dropwise addition, the mixture was stirred at room temperature for 1 hour and then 91 g of N,N-dimethylformamide (DMF) was added dropwise thereto. After the dropwise addition, this was further stirred at room temperature for 1 hour, mixed with 1,000 ml of 10% hydrochloric acid and again stirred for 1 hour. This was extracted with 1,000 ml of ethyl acetate, washed twice with saturated brine and then dried with anhydrous sodium sulfate. By evaporating the solvent, 125 g of 3,5-difluorobenzaldehyde was obtained.

Workup

  1. temperaturewas gently refluxed
  2. additionAfter the dropwise addition
  3. additionAfter the dropwise addition
  4. stirringthis was further stirred at room temperature for 1 hour
  5. stirringagain stirred for 1 hour
  6. extractionThis was extracted with 1,000 ml of ethyl acetate
  7. washwashed twice with saturated brine
  8. dry with materialdried with anhydrous sodium sulfate
  9. customBy evaporating the solvent

Sources & evidence

ORD record
ord-070b081c68d04c6fabe6731899f0347a
Source dataset
uspto-grants-2004_02
Patent number
US06693223B1

Reaction notes

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