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

HRID 1627960

반응식

HRID 1627960 반응식
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

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 233813-BromobenzonitrileHCID 66827Phenylboronic Acid

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 57417360Sodium chloride; water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-672f169e9bac4a0c82ccc3ac4420dc73
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785665B2

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