Diethylamine → (3'-Methanesulfonyl-biphenyl-4-yl)-methanol

HRID 1373693Notes

Reaction equation

HRID 1373693 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:3]=1.[OH:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(CC)CC.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.C(O)CC>[CH3:11][S:8]([C:4]1[CH:3]=[C:2]([C:17]2[CH:18]=[CH:19][C:14]([CH2:13][OH:12])=[CH:15][CH:16]=2)[CH:7]=[CH:6][CH:5]=1)(=[O:10])=[O:9]

Participants

10

Reactant 5

HCID 8021DiethylamineHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 2757146Benzene, 1-bromo-3-(methylsulfonyl)-

Product 1

HCID 21879230(3'-Methanesulfonyl-biphenyl-4-yl)-methanolYield 95.5%

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 10311-PropanolSolventHCID 1140TolueneSolvent

Procedure

To a degassed solution of the product of step 1 (5.7 g, 24.2 mmol,), and 4-hydroxymethylphenylboronic acid (5.47 g, 36 mmol) in toluene (150 mL) was added Pd2(dba)3 (1.09 g, 1.2 mmol). The mixture was degassed and Ph3P (2.5 g, 9.6 mmol), Et2NH (2.63 g, 36 mmol), n-propanol (18 mL) and H2O (18 mL) was added. The mixture was heated to reflux for 26 h. Aqueous NaHCO3 was added and the resulting mixture was extracted with EtOAc. The combined organic extracts were washed with brine, dried (anhyd. MgSO4) and concentrated in vacuo. The residue was purified by chromatography on silica gel to give 6.06 g (95%) of the title compound.

Workup

  1. customThe mixture was degassed
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 26 h
  4. extractionthe resulting mixture was extracted with EtOAc
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (anhyd. MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-606677831ed448d3a23675acd076e7ff
Source dataset
uspto-grants-2007_01
Patent number
US07163932B2

Reaction notes

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