1-Bromo-4-((methylsulfonyl)methyl)benzene → 4,4,5,5-Tetramethyl-2-(4'-((methylsulfonyl)methyl)-[1,1'-biphenyl]-4-yl)-1,3,2-dioxaborolane

HRID 1050237ノート

反応式

HRID 1050237 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:4][CH:3]=1.[CH3:13][C:14]1([CH3:36])[C:18]([CH3:20])([CH3:19])[O:17][B:16]([C:21]2[CH:26]=[CH:25][C:24](B3OC(C)(C)C(C)(C)O3)=[CH:23][CH:22]=2)[O:15]1>C1COCC1.C(=O)([O-])[O-].[Ag+2].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>[CH3:19][C:18]1([CH3:20])[C:14]([CH3:13])([CH3:36])[O:15][B:16]([C:21]2[CH:26]=[CH:25][C:24]([C:2]3[CH:7]=[CH:6][C:5]([CH2:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:4][CH:3]=3)=[CH:23][CH:22]=2)[O:17]1

参加物

6

反応物 2

HCID 27614151-Bromo-4-((methylsulfonyl)methyl)benzeneHCID 105924952,2'-(1,4-Phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

生成物 1

HCID 900593934,4,5,5-Tetramethyl-2-(4'-((methylsulfonyl)methyl)-[1,1'-biphenyl]-4-yl)-1,3,2-dioxaborolane

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 178418647HCID 178418647、化合物触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

1-bromo-4-((methylsulfonyl)methyl)benzene (1.5 g, 6.02 mmol), 1,4-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (4.97 g, 15.05 mmol), and silver carbonate (1.826 g, 6.62 mmol) were dissolved in THF (60.2 ml) and sparged with N2 for 15 min. Then Pd(PPh3)4 (0.348 g, 0.301 mmol) was added and the reaction was heated to 80° C. overnight. The reaction was then cooled to rt, filtered through Celite™ and concentrated in vacuo. The resulting residue was purified by column chromatography on a Biotage™ 50 g column by eluting with 5% to 50% EtOAc:Hex to yield the desired product. 1H NMR δ (ppm) 7.83 (d, 2H), 7.69 (d, 2H), 7.64 (d, 2H), 7.54 (d, 2H), 4.46 (s, 2H), 2.89 (s, 3H), 1.4 (12H).

後処理

  1. customsparged with N2 for 15 min
  2. temperatureThe reaction was then cooled to rt
  3. filtrationfiltered through Celite™
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by column chromatography on a Biotage™ 50 g column
  6. washby eluting with 5% to 50% EtOAc

出典と根拠

ORDレコード
ord-3ca29cbe1875486984f01544e6e6fc8e
出典データセット
uspto-grants-2016_07
特許番号
US09382243B2

反応ノート

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