Dimethylformamide → 3-Fluoro-4-methylbenzaldehyde

HRID 2231121Notes

Reaction equation

HRID 2231121 reaction equation
C([Li])(C)(C)C.Br[C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[C:9]([F:14])[CH:8]=1.CN(C)[CH:17]=[O:18].S(=O)(=O)(O)[O-].[K+]>C1(C)C=CC=CC=1.O1CCCC1>[F:14][C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][C:10]=1[CH3:13])[CH:17]=[O:18]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 1710404-Bromo-2-fluorotolueneHCID 516920Potassium bisulfateHCID 178418306HCID 178418306, compound

Product 1

HCID 27745743-Fluoro-4-methylbenzaldehydeYield 91.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

tert-Butyllithium (31 ml of a 1.7 M solution in toluene, 52 mmol) was added slowly over 30 minutes to a cold (−70° C.), stirred solution of 4-bromo-2-fluorotoluene (5 g, 26 mmol) in tetrahydrofuran (25 ml). After addition was complete, the mixture was stirred for 15 minutes and a solution of dimethylformamide (2 g, 28 mmol) in tetrahydrofuran (10 ml) was then added over 10 minutes. After addition was complete, the reaction solution was warmed to room temperature over 30 minutes. The reaction was poured into 0.5N aqueous potassium bisulfate (125 ml) and extracted with ethyl ether. The combined organic extracts were dried over sodium sulfate and evaporated to give 3.3 g (90%) of the desired product as an oil. This material was suitable for use without further purification.

Workup

  1. additionAfter addition
  2. additionAfter addition
  3. extractionextracted with ethyl ether
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-13fe33a9a18c4471b67d35de072bed84
Source dataset
uspto-grants-2002_07
Patent number
US06426360B1

Reaction notes

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