Triethylamine → [1,1'-Biphenyl]-3-carbonitrile

HRID 1627960

反応式

HRID 1627960 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CCN(CC)CC>O.[Cl-].[Na+].O>[C:10]1([C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=2)[C:5]#[N:6])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 233813-BromobenzonitrileHCID 66827Phenylboronic Acid

生成物 1

HCID 34340[1,1'-Biphenyl]-3-carbonitrile収率 93%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

3-Bromobenzonitrile (91 mg, 0.5 mmol), phenylboronic acid (91 mg, 0.75 mmol), and Pd(dtbpf)Cl2 (6 mg, 0.01 mmol) were added to a reaction tube equipped with a magnetic stir bar. Under a positive flow of argon while stirring, surfactant solution (1.0 mL, 2 wt % TPGS-M-PEG-750 in water), and Et3N (0.21 mL, 1.5 mmol) were added by syringe and stirred vigorously for 2 h. The reaction mixture was then diluted with brine and extracted with EtOAc. The solution obtained was dried over anhydrous MgSO4 and concentrated by rotary evaporation. The residue was purified by flash column chromatography eluting with 20% CH2Cl2/hexanes to afford the product (83 mg, 93%) as a slightly yellow oil.

後処理

  1. customequipped with a magnetic stir bar
  2. stirringstirred vigorously for 2 h
  3. extractionextracted with EtOAc
  4. customThe solution obtained
  5. dry with materialwas dried over anhydrous MgSO4
  6. concentrationconcentrated by rotary evaporation
  7. customThe residue was purified by flash column chromatography
  8. washeluting with 20% CH2Cl2/hexanes

出典と根拠

ORDレコード
ord-672f169e9bac4a0c82ccc3ac4420dc73
出典データセット
uspto-grants-2014_07
特許番号
US08785665B2

関連ノート

読み込み中…