Sodium Carbonate → HCID 10620805、化合物

HRID 343253ノート

反応式

HRID 343253 の反応式
[F:1][C:2]1[C:7]([F:8])=[C:6]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:5]=[CH:4][C:3]=1B(O)O.[Br:21][C:22]1[CH:27]=[CH:26][C:25](I)=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.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:21][C:22]1[CH:27]=[CH:26][C:25]([C:3]2[CH:4]=[CH:5][C:6]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[C:7]([F:8])[C:2]=2[F:1])=[CH:24][CH:23]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 115221-Bromo-4-iodobenzene2 回HCID 10850744(2,3-Difluoro-4-(octyloxy)phenyl)boronic acid

生成物 1

HCID 10620805HCID 10620805、化合物

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒2 回

実験手順

A solution of 2,3-difluro-4-octoxyphenylboronic acid (5) (8.29 g, 0.029 mol) in dimethoxyethane (40 ml) was added to a solution of 4-bromoiodobenzene (6.80 g, 0.024 mol) and tetrakis(triphenylphosphine)palladium (0) (1.4 8 g. 1.29 mmol) in dimethoxyethane (40 ml) under nitrogen. To this, 2M sodium carbonate (60 ml) was added. The stirred mixture was refluxed gently. Progress of the reaction was carefully monitored using tic until the 4-bromoiodobenzene had reacted completely (usually 4-5hr). The layers were separated and the aqueous layer once more extracted with ether. The combined organic layers were washed with brine and dried (MgSO4). The solvent was removed in vacuo and the residue purified by column chromatography (silica gel/petroleum fraction (bp 40°-60° C.) - ethyl acetate, 9:1) to give a white solid which was recrystallised from pentane (-20° C.) to yield colourless crystals.

後処理

  1. temperatureThe stirred mixture was refluxed gently
  2. customhad reacted completely (usually 4-5hr)
  3. customThe layers were separated
  4. extractionthe aqueous layer once more extracted with ether
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. customThe solvent was removed in vacuo
  8. customthe residue purified by column chromatography (silica gel/petroleum fraction (bp 40°-60° C.) - ethyl acetate, 9:1)
  9. customto give a white solid which
  10. customwas recrystallised from pentane (-20° C.)
  11. customto yield colourless crystals

出典と根拠

ORDレコード
ord-66e3316ba47240538a7c235187b81555
出典データセット
uspto-grants-1999_01
特許番号
US05861109

反応ノート

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