Sodium Carbonate → [1,1':2',1''-Terphenyl]-2-amine

HRID 348584ノート

反応式

HRID 348584 の反応式
Br[C:2]1[CH:8]=[CH:7][CH:6]=[C:5](Br)[C:3]=1[NH2:4].[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CCO.O.CCOCC.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>[C:2]1([C:11]2[C:10]([C:2]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:3]=3)=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:3]([NH2:4])=[CH:5][CH:6]=[CH:7][CH:8]=1

参加物

9

反応物 3

HCID 10340Sodium Carbonate2 回HCID 66827Phenylboronic AcidHCID 690982,6-Dibromoaniline

生成物 1

HCID 12595497[1,1':2',1''-Terphenyl]-2-amine収率 90%

試薬・触媒・溶媒 5

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒

実験手順

2,6-Dibromoaniline (6.02 g, 24 mmol) and Pd(PPh3)4 (3.88 g, 3.00 mmol) were dissolved in toluene (240 ml). Phenyl boronic acid (8.80 g, 72 mmol) in EtOH (50 ml) was added. Na2CO3 (13 g, 144 mmol) in H2O (70 ml) was added. The reaction mixture was reflux for 24 hrs. The organic layer was thin separated and the amine precipitated as hydrochloride salt by addition of 20 ml of HCl. The precipitate was isolated. The salt was suspended in ether, and 2 M Na2CO3 was added. The organic layer was dried over Na2SO4 and the solvent was evaporated. The yield was 90%. 1H NMR (CDCl3): δ 7.44 (t, 4H, Harom), 7.39 (t, 4H, Harom), 7.29 (d, 2H, Harom), 7.07 (d, 2H, Harom), 6.82 (t, 1H, Harom), 3.77 (s, 2H, NH2).

後処理

  1. temperatureThe reaction mixture was reflux for 24 hrs
  2. customThe organic layer was thin separated
  3. customthe amine precipitated as hydrochloride salt by addition of 20 ml of HCl
  4. customThe precipitate was isolated
  5. dry with materialThe organic layer was dried over Na2SO4
  6. customthe solvent was evaporated

出典と根拠

ORDレコード
ord-32f1229f4af7448c84f5f11bab7404b8
出典データセット
uspto-grants-2007_02
特許番号
US07176950B2

反応ノート

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