Hydrochloric Acid → 2,3-Difluoro-4-(4-pentylphenyl)-6-methylbenzaldehyde

HRID 1012905Notes

Reaction equation

HRID 1012905 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH3:20])[CH:5]=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:11][CH:10]=2)[C:7]=1[F:8].[Li]C(CC)C.CN([CH:29]=[O:30])C.Cl>C1COCC1>[F:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:11][CH:10]=2)[CH:5]=[C:4]([CH3:20])[C:3]=1[CH:29]=[O:30]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 231188243,4-Difluoro-5-(4-pentylphenyl)tolueneHCID 178418400CID 53628100

Product 1

HCID 231188322,3-Difluoro-4-(4-pentylphenyl)-6-methylbenzaldehydeYield 77.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under a nitrogen atmosphere, 8.93 g of the compound (22) having been dissolved in 66 mL of THF was cooled to −78° C., to which 39.0 mL of sec-BuLi (1 M/L) was added, followed by stirring at the same temperature for 2 hours. 3.56 g of DMF having been dissolved in 44 mL of THF was added thereto, followed by stirring at −78° C. for 1 hour, and after increasing the temperature to room temperature, stirring over night. 20 mL of 3N hydrochloric acid was added thereto, and the aqueous layer was extracted with toluene, which was added to the organic layer. The organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled off to obtain 7.61 g of 2,3-difluoro-4-(4-pentylphenyl)-6-methylbenzaldehyde (23).

Workup

  1. additionwas added
  2. additionwas added
  3. stirringby stirring at −78° C. for 1 hour
  4. stirringstirring over night
  5. extractionthe aqueous layer was extracted with toluene, which
  6. additionwas added to the organic layer
  7. washThe organic layer was washed with saturated saline
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-2a5939a7c7f74282866803b5cbfeab3f
Source dataset
uspto-grants-2011_07
Patent number
US07981486B2

Reaction notes

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