Sodium Carbonate → 4-Bromo-4'-(diphenylamino)biphenyl

HRID 1618830

反応式

HRID 1618830 の反応式
[C:1]1([N:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:8]2[CH:13]=[CH:12][C:11](B(O)O)=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[C:24]1[CH:29]=[CH:28][C:27]([Br:30])=[CH:26][CH:25]=1.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.O.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>[Br:30][C:27]1[CH:28]=[CH:29][C:24]([C:11]2[CH:12]=[CH:13][C:8]([N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:9][CH:10]=2)=[CH:25][CH:26]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 115221-Bromo-4-iodobenzeneHCID 121669344-(Diphenylamino)phenylboronic Acid (contains varying amounts of Anhydride)

生成物 1

HCID 113155504-Bromo-4'-(diphenylamino)biphenyl収率 87%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 21881883Oxolane--water (1/1)溶媒

実験手順

A mixture of (4-(diphenylamino)phenyl)boronic acid (1.5 g, 5.19 mmol), 4-iodo-1-bromobenzene (1.33 g, 4.71 mmol), Na2CO3 (1.78 g, 16.8 mmol) and Pd(PPh3)4 (0.163 g, 0.141 mmol) in THF/H2O (28 mL/17 mL) was degassed and the resulting mixture was heated at reflux overnight under an argon atmosphere. After cooling, the mixture was poured into dichloromethane (150 mL), then washed with water (2×150 mL) and brine (100 mL). The organic phase was dried over Na2SO4, purified with flash column chromatography (silica gel, hexanes/ethyl acetate 50:1) then recrystallized in dichloromethane/methanol to afford a white solid (Compound 35)(1.64 g, in 87% yield).

後処理

  1. customwas degassed
  2. temperaturethe resulting mixture was heated
  3. temperatureat reflux overnight under an argon atmosphere
  4. temperatureAfter cooling
  5. additionthe mixture was poured into dichloromethane (150 mL)
  6. washwashed with water (2×150 mL) and brine (100 mL)
  7. dry with materialThe organic phase was dried over Na2SO4
  8. custompurified with flash column chromatography (silica gel, hexanes/ethyl acetate 50:1)
  9. customthen recrystallized in dichloromethane/methanol

出典と根拠

ORDレコード
ord-d9dab75fdf0149dc920fa6231f79db7c
出典データセット
uspto-grants-2014_07
特許番号
US08771845B2

関連ノート

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