Hydrochloric Acid → HCID 58077434, compound

HRID 387237Notes

Reaction equation

HRID 387237 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH3:16])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C1C[O:20][CH2:19]C1.C([Li])(CC)C.Cl>C1(C)C=CC=CC=1.CN(C)C=O.CCCCCC.C1CCCCC1>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH3:16])=[CH:10][CH:9]=2)[CH:5]=[CH:6][C:7]=1[CH:19]=[O:20]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 185211083-Fluoro-4'-propylbiphenylHCID 178418400CID 53628100

Product 1

HCID 58077434HCID 58077434, compound

Reagents, catalysts & solvents 4

HCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8078CyclohexaneSolvent

Conditions

Temperature
-74 °C

Procedure

In a reaction vessel under a nitrogen atmosphere, 27.0 g of 3-fluoro-4′-propylbiphenyl (T-1) and 270 ml of THF were put, and cooled to −74° C. Thereto, 141 ml of cyclohexane and n-hexane solution of 1.07 M sec-butyllithium was added dropwise in a temperature range of −74° C. to −65° C., and stirred for another 120 minutes. Subsequently, 19.5 ml of N,N-dimethylformamide (DMF) was added dropwise in a temperature range of −74° C. to −67° C., and stirred for another 60 minutes. The reaction mixture obtained was returned to 25° C., and then poured into 300 ml of 0.1 N hydrochloric acid solution and mixed. Then 300 ml of toluene was added, and allowed to be separated into an organic layer and an aqueous layer, and extraction was carried out. Then the organic layer obtained was washed successively with water, a saturated aqueous solution of sodium hydrogencarbonate and water, and dried over anhydrous magnesium sulfate. The solution obtained was concentrated under reduced pressure, and the residue was purified by column chromatography (silica gel; heptane/toluene (=1/1 by volume)) to obtain 29.6 g of 3-fluoro-4′-propylbiphenyl-4-carbaldehyde (T-2). The yield based on compound (T-1) was 97%.

Workup

  1. stirringstirred for another 60 minutes
  2. customThe reaction mixture obtained
  3. customwas returned to 25° C.
  4. additionmixed
  5. customto be separated into an organic layer
  6. extractionan aqueous layer, and extraction
  7. customThen the organic layer obtained
  8. washwas washed successively with water
  9. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and water, and dried over anhydrous magnesium sulfate
  10. customThe solution obtained
  11. concentrationwas concentrated under reduced pressure
  12. customthe residue was purified by column chromatography (silica gel; heptane/toluene (=1/1 by volume))

Sources & evidence

ORD record
ord-c7680df063f24eef82970cf1b05f110c
Source dataset
uspto-grants-2013_02
Patent number
US08372975B2

Reaction notes

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