Dimethylformamide → HCID 86626909, compound

HRID 604177Notes

Reaction equation

HRID 604177 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([O:12][CH3:13])=[CH:4][C:3]=1[C:14]1[CH:19]=[C:18]([CH:20]([CH3:22])[CH3:21])[CH:17]=[CH:16][C:15]=1[O:23][CH3:24].C([Li])CCC.CN(C)[CH:32]=[O:33].[Cl-].[NH4+]>O1CCCC1.CCCCCC.C(OCC)(=O)C>[CH:20]([C:18]1[CH:17]=[CH:16][C:15]([O:23][CH3:24])=[C:14]([C:3]2[C:2]([CH:32]=[O:33])=[CH:7][C:6]([C:8]([F:9])([F:11])[F:10])=[C:5]([O:12][CH3:13])[CH:4]=2)[CH:19]=1)([CH3:22])[CH3:21]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 66602988HCID 66602988, compoundHCID 178418339Butyllithium

Product 1

HCID 86626909HCID 86626909, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Bromo-5′-isopropyl-5,2′-dimethoxy-4-trifluoromethyl-biphenyl (1.29 g) is dissolved in dry tetrahydrofuran (30 ml) and thereto is added dropwise 1.6M n-butyllithium in hexane at −78° C., and the mixture is stirred for 1 hour and thereto is added N,N-dimethylformamide (1.2 ml), and the mixture is stirred for 1.5 hours. To the reaction solution are added a saturated aqueous ammonium chloride solution and ethyl acetate, and the mixture is separated, and the organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=49:1→17:3) to give 5′-isopropyl-5,2′-dimethoxy-4-trifluoromethyl-biphenyl-2-carbaldehyde (733 mg). MS (m/z): 353 [M+H]+

Workup

  1. stirringthe mixture is stirred for 1.5 hours
  2. customthe mixture is separated
  3. washthe organic layer is washed with a saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=49:1→17:3)

Sources & evidence

ORD record
ord-5d6cd1e3f73b45b6897168dc080a8898
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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