Potassium Carbonate → Tert-butyl 4'-methyl-5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]biphenyl-3-carboxylate

HRID 888369ノート

反応式

HRID 888369 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([C:15]([OH:24])([C:20]([F:23])([F:22])[F:21])[C:16]([F:19])([F:18])[F:17])[CH:14]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[CH3:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1.C([O-])([O-])=O.[K+].[K+]>C(O)CC.O>[CH3:25][C:26]1[CH:31]=[CH:30][C:29]([C:2]2[CH:14]=[C:13]([C:15]([OH:24])([C:20]([F:21])([F:22])[F:23])[C:16]([F:17])([F:19])[F:18])[CH:12]=[C:4]([C:5]([O:7][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:6])[CH:3]=2)=[CH:28][CH:27]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 79799Tolylboronic acidHCID 86646752Tert-butyl 3-bromo-5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzoate

生成物 1

HCID 86646751Tert-butyl 4'-methyl-5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]biphenyl-3-carboxylate

試薬・触媒・溶媒 1

HCID 22595341Propanol water溶媒

反応条件

温度
85 °C

実験手順

To a mixture of tert-butyl 3-bromo-5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzoate (1.2 g, 2.8 mmol) from Example 2.11 step B, (4-methylphenyl)boronic acid (0.5 g, 3.7 mmol), Pd[P(Ph3)]4 (0.16 g, 0.14 mmol), and K2CO3 (1.2 g, 8.5 mmol) under N2 was added 28 mL of degassed n-Propanol/water (4:1). The reaction was heated to 85° C. overnight. The mixture was cooled to room temperature, filtered over celite and concentrated. The crude material was taken up in EtOAc and sat. NaHCO3. The organic layer was extracted (3×) and washed with brine. The final organic layer was dried over Na2SO4, filtered and concentrated to 1.0 g of crude material. Purification using automated flash chromatography (SiO2, 120 g, 0-5% MeOH/DCM) gave, upon concentration, title product.

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered over celite and
  3. concentrationconcentrated
  4. extractionThe organic layer was extracted (3×)
  5. washwashed with brine
  6. dry with materialThe final organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated to 1.0 g of crude material
  9. customPurification

出典と根拠

ORDレコード
ord-f965fd1624894df19409446d99519014
出典データセット
uspto-grants-2012_08
特許番号
US08247401B2

反応ノート

読み込み中…