Isopropyl iodide → 6-Bromo-2,4'-difluoro-3-isopropoxybiphenyl-4-carbaldehyde

HRID 2272528Notes

Reaction equation

HRID 2272528 reaction equation
I[CH:2]([CH3:4])[CH3:3].[Br:5][C:6]1[C:11]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[C:10]([F:19])[C:9]([OH:20])=[C:8]([CH:21]=[O:22])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:5][C:6]1[C:11]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[C:10]([F:19])[C:9]([O:20][CH:2]([CH3:4])[CH3:3])=[C:8]([CH:21]=[O:22])[CH:7]=1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 904231046-Bromo-2,4'-difluoro-3-hydroxybiphenyl 4 carbaldehyde

Product 1

HCID 1179922366-Bromo-2,4'-difluoro-3-isopropoxybiphenyl-4-carbaldehydeYield 94.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Iodopropane (21.7 g) was added to a mixture of 6-bromo-2,4′-difluoro-3-hydroxybiphenyl-4-carbaldehyde (26.7 g) and potassium carbonate (23.6 g) in DMF (250 mL) at room temperature. The mixture was stirred at 60 C under nitrogen atmosphere for 3 hours. The mixture was quenched with water at room temperature and extracted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by a silica gel column chromatography (hexane/ethyl acetate) to give the title compound (28.5 g).

Workup

  1. customThe mixture was quenched with water at room temperature
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by a silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-81a130098aec4cac882155a5a0dcce3a
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

Loading…