Iodoethane → HCID 117992075, compound

HRID 531141Notes

Reaction equation

HRID 531141 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[O:16])=[C:11]([OH:17])[CH:10]=1.I[CH2:19][CH3:20].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:19]([O:17][C:11]1[CH:10]=[C:9]([C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])[CH:14]=[CH:13][C:12]=1[CH:15]=[O:16])[CH3:20]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 532203732',4'-Difluoro-3-hydroxy[1,1'-biphenyl]-4-carbaldehyde

Product 1

HCID 117992075HCID 117992075, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2′,4′-difluoro-3-hydroxybiphenyl-4-carbaldehyde (8.00 g), iodoethane (8.98 g) and potassium carbonate (6.19 g) in acetone (70 mL) was stirred at 60° C. for 3 hours. The mixture was filtered through celite. The filtrate was concentrated in vacuo. The residue was diluted with ethyl acetate and water. The organic layer was separated and concentrated in vacuo. The residue was refluxed for 30 minutes in methanol (30 mL), cooled to room temperature, and further stirred for 1 hour. The solid was collected by filtration, washed with methanol (10 mL) and dried at 70° C. to give the title compound (5.16 g).

Workup

  1. filtrationThe mixture was filtered through celite
  2. concentrationThe filtrate was concentrated in vacuo
  3. additionThe residue was diluted with ethyl acetate and water
  4. customThe organic layer was separated
  5. concentrationconcentrated in vacuo
  6. temperatureThe residue was refluxed for 30 minutes in methanol (30 mL)
  7. temperaturecooled to room temperature
  8. stirringfurther stirred for 1 hour
  9. filtrationThe solid was collected by filtration
  10. washwashed with methanol (10 mL)
  11. customdried at 70° C.

Sources & evidence

ORD record
ord-7f4d482bef6b459c888f81272c74e5d2
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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