Sodium Carbonate → (2'-Chloro-3-methylbiphenyl-4-yl)methanol

HRID 2194880Notes

Reaction equation

HRID 2194880 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[C:4]([CH3:10])[CH:3]=1.[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>C(O)CC.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[C:4]([CH3:10])[CH:3]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27343222-Chlorophenylboronic acidHCID 22280088(4-Bromo-2-methylphenyl)methanol

Product 1

HCID 67448566(2'-Chloro-3-methylbiphenyl-4-yl)methanol

Reagents, catalysts & solvents 3

HCID 11554889palladium acetate PPh3CatalystHCID 962WaterSolventHCID 10311-PropanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution (4-bromo-2-methylphenyl)methanol (1 eq.) from Benzyl nitrile III.1 (Step 1) and 2-chlorophenylboronic acid (1.2 eq.) in n-propanol (0.1M) was added palladium acetate/triphenyl phosphine (1:3; 0.05 eq.) and aqueous Na2CO3 (2M; 3 eq.). The mixture was stirred at 80° C. for 2 h, cooled to room temperature, poured in water and extracted with EtOAc. The organic extract was washed with, brine, dried over MgSO4 filtered and concentrated. Purification by column chromatography on silica gel (Combi-Flash by ISCO), eluting with Hex/EtOAc (0 to 75% in 30 min) to afforded the desired compound.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with EtOAc
  3. extractionThe organic extract
  4. washwas washed with, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by column chromatography on silica gel (Combi-Flash by ISCO)
  9. washeluting with Hex/EtOAc (0 to 75% in 30 min)

Sources & evidence

ORD record
ord-d9bba7d36a6d4d7093e4d41c531001d7
Source dataset
uspto-grants-2012_12
Patent number
US08334308B2

Reaction notes

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