Potassium Carbonate → 2,6-Bis(3-pyridyl)phenyl benzyl ether

HRID 2069874ノート

反応式

HRID 2069874 の反応式
[CH2:1]([O:8][C:9]1[C:14](Br)=[CH:13][CH:12]=[CH:11][C:10]=1Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:17]1[CH:22]=[CH:21][CH:20]=[C:19](B(O)O)[CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C=O)C>[CH2:1]([O:8][C:9]1[C:14]([C:19]2[CH:18]=[N:17][CH:22]=[CH:21][CH:20]=2)=[CH:13][CH:12]=[CH:11][C:10]=1[C:19]1[CH:18]=[N:17][CH:22]=[CH:21][CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 27343783-Pyridinylboronic acidHCID 145344892-(Benzyloxy)-1,3-dibromobenzene

生成物 1

HCID 581502802,6-Bis(3-pyridyl)phenyl benzyl ether収率 41%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
85 °C

実験手順

2,6-Dibromophenyl benzyl ether (25.61 g, 74.88 mmol), 3-pyridylboronicacid (20.25 g, 164.7 mmol), aqueous potassium carbonate (233 mL 2 M), and DMF (370 mL) were put together in a 1 liter flask. Oxygen was removed by several vacuum-argon cycles. Then Pd(PPh3)4 (5.38 g, 4.65 mmol) was added and the mixture was heated to 85° C. under an argon atmosphere. After 48 hr, the reaction mixture was cooled to rt, and poured into an ice/water mixture (1 L). This was extracted with diisopropylether (3 times 300 mL), and the combined organic layers were dried over MgSO4, filtered, and the solvent was removed in vacuo, yielding a yellow crystalline solid. Recrystallisation from diethyl ether yielded the product as a white crystalline solid (10.34 g, 41%). The residue was further purified by column chromatography (silicagel, EtOAc/n-pentane=3:2), yielding another 2.60 g (10%) of the product (total yield 51%). 1H-NMR(CDCl3):δ=8.80 (s, 2H), 8.59 (d, 2H), 7.93 (dd, 2H), 7.65 (d, 2H), 7.34 (m, 3H), 7.19 (t, 1H), 7.10 (t, 2H), 6.64 (d, 2H), 4.15 (s, 2H) ppm.

後処理

  1. customOxygen was removed by several vacuum-argon cycles
  2. temperaturethe reaction mixture was cooled to rt
  3. extractionThis was extracted with diisopropylether (3 times 300 mL)
  4. dry with materialthe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo
  7. customyielding a yellow crystalline solid
  8. customRecrystallisation from diethyl ether

出典と根拠

ORDレコード
ord-3aabeaefb4ad412cbc04944299d36e5e
出典データセット
uspto-grants-2012_10
特許番号
US08299202B2

反応ノート

読み込み中…