Sodium Carbonate → HCID 1393595、化合物

HRID 1879253ノート

反応式

HRID 1879253 の反応式
[OH:1][CH2:2][C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1.[Br:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15](I)[CH:14]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[Br:12][C:13]1[CH:14]=[C:15]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([CH2:2][OH:1])[CH:4]=2)[CH:16]=[CH:17][CH:18]=1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 11561Benzene, 1-bromo-3-iodo-HCID 2734662[3-(Hydroxymethyl)phenyl]boronic acid

生成物 1

HCID 1393595HCID 1393595、化合物収率 80%

試薬・触媒・溶媒 3

HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

To a 0.2 M solution of [3-(hydroxymethyl)phenyl]boronic acid in DME were sequentially added 1-bromo-3-iodobenzene (0.83 eq.) and a 2M solution of Na2CO3 (3.0 eq.). The reaction mixture was degassed, trans-bis(triphenylphosphine)palladium(II) chloride (0.01 eq.) was added and it was stirred at 80° C. for 6 h. After cooling down to RT the reaction mixture was diluted with EtOAc and washed with saturated aq. NaHCO3, 1N HCl and brine. The residue was dried (Na2SO4) and evaporated under reduced pressure to afford an oil which was purified by flash chromatography (SiO2, PE:EtOAc=8:2) to afford the title compound 94 as an oil (80%). 1H NMR (400 MHz, DMSO-d6, 300 K) δ 7.87 (s, 1H), 7.71 (d, J 7.7, 1H), 7.66 (bs, 1H), 7.59 (t, J 6.8, 2H), 7.47 (t, J 7.7, 2H), 7.39 (d, J 7.7, 1H), 4.61 (s, 2H).

後処理

  1. customThe reaction mixture was degassed
  2. temperatureAfter cooling down to RT the reaction mixture
  3. washwashed with saturated aq. NaHCO3, 1N HCl and brine
  4. dry with materialThe residue was dried (Na2SO4)
  5. customevaporated under reduced pressure
  6. customto afford an oil which
  7. customwas purified by flash chromatography (SiO2, PE:EtOAc=8:2)

出典と根拠

ORDレコード
ord-24ffda31d254463b9b2c7c2a8f9e437f
出典データセット
uspto-grants-2012_11
特許番号
US08314062B2

反応ノート

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