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

HRID 2272509Notes

Reaction equation

HRID 2272509 reaction equation
[Br:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)=[C:6]([F:15])[C:5]([OH:16])=[C:4]([CH:17]=[O:18])[CH:3]=1.I[CH:20]([CH3:22])[CH3:21].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[Br:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)=[C:6]([F:15])[C:5]([O:16][CH:20]([CH3:22])[CH3:21])=[C:4]([CH:17]=[O:18])[CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 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 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6-bromo-2,4′-difluoro-3-hydroxybiphenyl-4-carbaldehyde (3.50 g), 2-iodopropane (5.70 g), potassium carbonate (3.09 g), and DMF (15 mL) was stirred at 50 C for 1 hour. The reaction mixture was poured to water, followed by extraction with ethyl acetate twice. The organic layer was separated, then washed with saturated saline, and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (2.94 g)

Workup

  1. extractionfollowed by extraction with ethyl acetate twice
  2. customThe organic layer was separated
  3. washwashed with saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-3de6f149ed1641a2829a8e728b24b337
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

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