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

HRID 2194880ノート

反応式

HRID 2194880 の反応式
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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 11554889palladium acetate PPh3触媒HCID 962Water溶媒HCID 10311-Propanol溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-d9bba7d36a6d4d7093e4d41c531001d7
出典データセット
uspto-grants-2012_12
特許番号
US08334308B2

反応ノート

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