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Iodoethane → 6-Bromo-3-ethoxy-2,4'-difluorobiphenyl-4-carbaldehyde

HRID 531110
Notes
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Reaction equation

HRID 531110 reaction equation
I[CH2:2][CH3:3].[Br:4][C:5]1[C:10]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[C:9]([F:18])[C:8]([OH:19])=[C:7]([CH:20]=[O:21])[CH:6]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:4][C:5]1[C:10]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[C:9]([F:18])[C:8]([O:19][CH2:2][CH3:3])=[C:7]([CH:20]=[O:21])[CH:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 904231046-Bromo-2,4'-difluoro-3-hydroxybiphenyl 4 carbaldehyde

Product 1

HCID 904237546-Bromo-3-ethoxy-2,4'-difluorobiphenyl-4-carbaldehydeYield 95.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Iodoethane (2.54 g) was added to a mixture of 6-Bromo-2,4′-difluoro-3-hydroxybiphenyl-4-carbaldehyde (3.40 g) and potassium carbonate (3.00 g) in DMF (35 mL) at room temperature. The mixture was stirred at 60° C. under nitrogen atmosphere for 5 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 (3.55 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-22758b3ed1564a8ea94118d1afa4c1ef
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09353108B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes