Hydrochloric Acid → Bis(3,5-di-t-butyl-4-methoxyphenyl)(2-bromophenyl)phosphine oxide

HRID 1581623ノート

反応式

HRID 1581623 の反応式
[C:1]([C:5]1[CH:6]=[C:7]([PH:17](=[O:34])[C:18]2[CH:23]=[C:22]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:21]([O:28][CH3:29])=[C:20]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH:19]=2)[CH:8]=[C:9]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:10]=1[O:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C1(PCCCPC2C=CC=CC=2)C=CC=CC=1.FC(F)(F)S(O[C:76]1[CH:81]=[CH:80][CH:79]=[CH:78][C:77]=1[Br:82])(=O)=O.C(N(CC)C(C)C)(C)C.Cl>C1(C)C=CC=CC=1>[C:24]([C:22]1[CH:23]=[C:18]([P:17](=[O:34])([C:7]2[CH:8]=[C:9]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:10]([O:11][CH3:12])=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[CH:6]=2)[C:76]2[CH:81]=[CH:80][CH:79]=[CH:78][C:77]=2[Br:82])[CH:19]=[C:20]([C:30]([CH3:33])([CH3:32])[CH3:31])[C:21]=1[O:28][CH3:29])([CH3:27])([CH3:26])[CH3:25]

参加物

8

反応物 6

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 95417Dibenzylidene acetoneHCID 43668911,3-Bis(phenylphosphino)propaneHCID 149827202-Bromophenyl TrifluoromethanesulfonateHCID 178490127HCID 178490127、化合物

生成物 1

HCID 12115809Bis(3,5-di-t-butyl-4-methoxyphenyl)(2-bromophenyl)phosphine oxide収率 97.7%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

Into a four-neck flask were weighed 28.71 g (59.0 mmol) of bis(3,5-di-t-butyl-4-methoxyphenyl)phosphine oxide, 1.27 g (2.5 mmol) of Pd2(dba)3CHCl3 (dba represents dibenzylideneacetone), and 1.01 g (2.5 mmol) of 1,3-diphenylphosphinopropane. The atmosphere of the reaction vessel which was fitted with a thermometer, a condenser tube, and a dropping funnel with a pressure-equalizing tube was completely replaced with nitrogen. Thereto were added 150 mL of toluene, 15.00 g (49.2 mmol) of the 2-(trifluoromethanesulfonyl)oxy-bromobenzene (5), and 9.53 g (73.8 mmol) of N,N-diisopropylethylamine, followed by 16 hours of heating at reflux. After the completion of the reaction, the reaction mixture was cooled to room temperature and poured into 150 mL of 5% hydrochloric acid aqueous solution. After 30 minutes of stirring, the layers were separated from each other. The organic layer was washed with water and brine and dried over anhydrous magnesium sulfate. Toluene was removed by evaporation and the residue was purified by silica gel column chromatography to obtain the title compound (30.83 g, a white viscous solid). Yield 97.7%.

後処理

  1. customInto a four-neck flask were weighed
  2. customThe atmosphere of the reaction vessel which was fitted with a thermometer, a condenser tube, and a dropping funnel with a pressure-equalizing tube
  3. temperatureof heating
  4. temperatureat reflux
  5. customAfter the completion of the reaction
  6. customthe layers were separated from each other
  7. washThe organic layer was washed with water and brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customToluene was removed by evaporation
  10. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-f929f0d1b5914934bb7af57111d183ed
出典データセット
uspto-grants-2004_05
特許番号
US06730629B2

反応ノート

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