Ammonium Chloride → HCID 18668652, compound

HRID 1059161Notes

Reaction equation

HRID 1059161 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[C:10]([CH:16]=[O:17])[CH:9]=2)=[CH:4][CH:3]=1.[CH:18]([Mg]Br)([CH3:20])[CH3:19].[Cl-].[NH4+]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[C:10]([CH:16]([OH:17])[CH:18]([CH3:20])[CH3:19])[CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 223912344'-Fluoro-6-methoxy[1,1'-biphenyl]-3-carbaldehydeHCID 178418365HCID 178418365, compound

Product 1

HCID 18668652HCID 18668652, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4′-fluoro-6-methoxy[1,1′-biphenyl]-3-carbaldehyde (5.00 g) in THF (80 ml) was added dropwise a solution (0.63; 44.8 ml) of isopropylmagnesium bromide in THF at 0° C., and the mixture was stirred for 1 h 45 min. To the reaction mixture was added saturated aqueous ammonium chloride solution and the mixture was extracted with ethyl acetate, washed with saturated brine and dried. The solvent was evaporated under reduced pressure and the residue was purified by column chomatography (eluent, hexane:ethyl acetate=6:1→2:1) to give the title compound (3.82 g) as a yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed with saturated brine
  3. customdried
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by column chomatography (eluent, hexane:ethyl acetate=6:1→2:1)

Sources & evidence

ORD record
ord-ec662821410a41ac836856c823933746
Source dataset
uspto-grants-2003_02
Patent number
US06518257B1

Reaction notes

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