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

HRID 2194880노트

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HRID 2194880 반응식
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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 11554889palladium acetate PPh3촉매HCID 962Water용매HCID 10311-Propanol용매

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온도
80 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d9bba7d36a6d4d7093e4d41c531001d7
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08334308B2

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