Sodium Carbonate → 4-Fluoro-3'-methoxy-3-nitrobiphenyl

HRID 49129ノート

反応式

HRID 49129 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1.Br[C:13]1[CH:14]=[CH:15][C:16]([F:22])=[C:17]([N+:19]([O-:21])=[O:20])[CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.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>[F:22][C:16]1[CH:15]=[CH:14][C:13]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:18][C:17]=1[N+:19]([O-:21])=[O:20]

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 2734370(3-Methoxyphenyl)boronic acidHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

生成物 1

HCID 104907024-Fluoro-3'-methoxy-3-nitrobiphenyl収率 77%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

Tetrakis(triphenylphosphine)palladium (0.7 g) was added to a mixture of 3.8 g of 3-methoxyphenylboronic acid, 5 g of 5-bromo-2-fluoronitrobenzene and 11 mL of 2M sodium carbonate solution in 100 mL of toluene. The mixture was heated to reflux for 2 hours, diluted with water and extracted with ethyl acetate. The ethyl acetate was washed with saturated sodium bicarbonate, brine, dried, and concentrated to give an oily solid. The solid was purified by column chromatography on silica gel in ethyl acetate:hexane 1:6 to give 4.3 g (77% yield) of 4-fluoro-3′-methoxy-3-nitrobiphenyl.

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hours
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate was washed with saturated sodium bicarbonate, brine
  5. customdried
  6. concentrationconcentrated
  7. customto give an oily solid
  8. customThe solid was purified by column chromatography on silica gel in ethyl acetate:hexane 1:6

出典と根拠

ORDレコード
ord-66dd4ba7c2f54d8aa9394a11c82c0559
出典データセット
uspto-grants-2004_03
特許番号
US06706709B2

反応ノート

読み込み中…