Hydrochloric Acid → 4-Fluoro-3-methylbenzaldehyde

HRID 2231134Notes

Reaction equation

HRID 2231134 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:9])=[C:6]([CH3:8])[CH:7]=1.C([Li])(C)(C)C.CN(C)[CH:17]=[O:18].Cl>O1CCCC1>[F:9][C:5]1[CH:4]=[CH:3][C:2]([CH:17]=[O:18])=[CH:7][C:6]=1[CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 1235275-Bromo-2-fluorotolueneHCID 178418306HCID 178418306, compound

Product 1

HCID 27348744-Fluoro-3-methylbenzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Bromo-2-fluoro-toluene (26 mmol, 5.0 g) was dissolved in tetrahydrofuran (25 ml) and cooled to −78° C. t-Butyllithium (1.7 M in pentane, 31 ml) was added over 10 minutes. After 30 minutes, N,N-dimethylformamide (2.1 ml) was added. The reaction mixture was warmed to ambient over 30 minutes and 6% HCl (100 ml) was added with vigorous swirling. The mixture was extracted with ethyl acetate (200 ml). The organic layer was dried over MgSO4, then concentrated affording the title compound as an oil (3.6 g, ˜quant.).

Workup

  1. additionwas added over 10 minutes
  2. temperatureThe reaction mixture was warmed
  3. waitto ambient over 30 minutes
  4. extractionThe mixture was extracted with ethyl acetate (200 ml)
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d31188e25a33402f82b8044733329eff
Source dataset
uspto-grants-2002_07
Patent number
US06426360B1

Reaction notes

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