Sodium Carbonate → 4'-Chloro-2'-methyl[1,1'-biphenyl]-3-carboxylic acid

HRID 2375737ノート

反応式

HRID 2375737 の反応式
I[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[Cl:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[C:14]([CH3:21])[CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].CC(O)C.O>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:2]2[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=[O:6])[CH:3]=2)=[C:14]([CH3:21])[CH:13]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 120603-Iodobenzoic acidHCID 5017600(4-Chloro-2-methylphenyl)boronic acid

生成物 1

HCID 462383924'-Chloro-2'-methyl[1,1'-biphenyl]-3-carboxylic acid

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 21889133Propan-2-ol--water (1/1)溶媒

反応条件

温度
80 °C

実験手順

To a mixture of 3-iodobenzoic acid (11.9 g, 48 mmol), 4-chloro-2-methylphenylboronic acid (9.8 g, 57.7 mmol) and sodium carbonate (6.1 g, 57.7 mmol) under nitrogen atmosphere, was added i-PrOH-water (1/1, 180 mL) followed by 10% Pd—C (2 g, 19.2 mmol) with caution. The reaction mixture was heated at 80° C. under nitrogen overnight. The catalyst was removed by filtration, and the filtered catalyst was washed with EtOH (60 mL). Most of organic solvent was removed under reduced pressure. The resulting aqueous residue was treated with 2N HCl (aq) to bring the pH <2. The resulting mixture was extracted with EtOAc (2×100 mL). The combined organic extracts were washed with water and saturated brine, dried over Na2SO4, filtered and concentrated under reduced pressure. Compound 9.7 was obtained as white solid (12 g), which was used directly in the next step. MS ESI (neg.) m/e: 245 (M−H).

後処理

  1. customThe catalyst was removed by filtration
  2. washthe filtered catalyst was washed with EtOH (60 mL)
  3. customMost of organic solvent was removed under reduced pressure
  4. additionThe resulting aqueous residue was treated with 2N HCl (aq)
  5. extractionThe resulting mixture was extracted with EtOAc (2×100 mL)
  6. washThe combined organic extracts were washed with water and saturated brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-827ffb44a3534db188100792d3e5677c
出典データセット
uspto-grants-2008_12
特許番号
US07465804B2

反応ノート

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