Dimethyl Sulfoxide → 2',6'-Dimethyl-4'-(3-(methylsulfonyl)propoxy)biphenyl-3-carbaldehyde

HRID 1848777Notes

Reaction equation

HRID 1848777 reaction equation
Br[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][CH2:10][CH2:11][CH2:12][S:13]([CH3:16])(=[O:15])=[O:14])=[CH:4][C:3]=1[CH3:17].[CH:18]([C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1)=[O:19].P([O-])([O-])([O-])=O.[K+].[K+].[K+].CS(C)=O>[C].[Pd].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[CH3:17][C:3]1[CH:4]=[C:5]([O:9][CH2:10][CH2:11][CH2:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH:6]=[C:7]([CH3:8])[C:2]=1[C:24]1[CH:23]=[CH:22][CH:21]=[C:20]([CH:18]=[O:19])[CH:25]=1

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 62657Potassium Phosphate, TribasicHCID 27343563-Formylphenylboronic acidHCID 709269352-Bromo-1,3-dimethyl-5-[3-(methylsulfonyl)propoxy]benzene

Product 1

HCID 593426022',6'-Dimethyl-4'-(3-(methylsulfonyl)propoxy)biphenyl-3-carbaldehydeYield 95.4%

Reagents, catalysts & solvents 3

HCID 634876Binap, (A+-)-CatalystHCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

2-Bromo-1,3-dimethyl-5-[3-(methylsulfonyl)propoxy]benzene (15.00 g), 3-formylphenylboronic acid (7.38 g), tripotassium phosphate (19.83 g), palladium carbon (3.0 g) and 2,2′-bis-(diphenylphosphino)-1,1′-binaphthyl (1.16 g) were added to dimethyl sulfoxide (150 mL) and water (75 mL), and the mixture was stirred at 80° C. for 5 hr. Activated carbon (1.5 g) was added, and the mixture was filtered with heating at 80° C. to remove the insoluble material. The filtrate was cooled to room temperature and stirred for 5 hr. The filtrate was cooled to 10° C. or below and stirred for 2 hr. Water (120 mL) was added dropwise, and the mixture was stirred for 1 hr. Water (150 mL) was added dropwise, and the mixture was stirred for 1 hr. The crystallized solid was collected by filtration, and the solid was washed with water (150 mL), and dried under reduced pressure to give 2′,6′-dimethyl-4′-[3-(methylsulfonyl)propoxy]biphenyl-3-carbaldehyde (15.43 g).

Workup

  1. additionActivated carbon (1.5 g) was added
  2. filtrationthe mixture was filtered
  3. temperaturewith heating at 80° C.
  4. customto remove the insoluble material
  5. temperatureThe filtrate was cooled to room temperature
  6. stirringstirred for 5 hr
  7. temperatureThe filtrate was cooled to 10° C. or below
  8. stirringstirred for 2 hr
  9. additionWater (120 mL) was added dropwise
  10. stirringthe mixture was stirred for 1 hr
  11. additionWater (150 mL) was added dropwise
  12. stirringthe mixture was stirred for 1 hr
  13. filtrationThe crystallized solid was collected by filtration
  14. washthe solid was washed with water (150 mL)
  15. customdried under reduced pressure

Sources & evidence

ORD record
ord-0565cb09069841f4a4e0acc67dad4a3b
Source dataset
uspto-grants-2015_02
Patent number
US08952185B2

Reaction notes

Loading…