Hydrochloric Acid → (2-Bromophenyl)[di(1-naphthyl)]phosphine

HRID 1168636

反応式

HRID 1168636 の反応式
[C:1]1([PH:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C1(P(CCC)C2C=CC=CC=2)C=CC=CC=1.FC(F)(F)S(O[C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][C:63]=1[Br:68])(=O)=O.C(N(C(C)C)CC)(C)C.Cl>C1(C)C=CC=CC=1>[Br:68][C:63]1[CH:64]=[CH:65][CH:66]=[CH:67][C:62]=1[P:11]([C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1)[C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

参加物

8

反応物 6

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 82100DiphenylpropylphosphineHCID 95417Dibenzylidene acetoneHCID 11737740Di-1-naphthalenylphosphineHCID 149827202-Bromophenyl Trifluoromethanesulfonate

生成物 1

HCID 11201532(2-Bromophenyl)[di(1-naphthyl)]phosphine収率 49.2%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

Into a four-neck flask were weighed 16.89 g (59.0 mmol) of di(1-naphthyl)phosphine, 1.27 g (2.5 mmol) of Pd2(dba)3CHCl3 (dba represents dibenzylideneacetone), and 1.01 g (2.5 mmol) of diphenylphosphinopropane. The atmosphere of the reaction vessel 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 2-(trifluoromethanesulfonyl)oxy-bromobenzene (5), and 9.53 g (73.8 mmol) of 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 saturated saline 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 (10.68 g, a pale yellow solid). Yield 49.2%.

後処理

  1. customInto a four-neck flask were weighed
  2. customThe atmosphere of the reaction vessel 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 saturated saline
  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-07dbfbf7c09447ed8cd0df60b0e9718b
出典データセット
uspto-grants-2003_09
特許番号
US06624320B2

関連ノート

読み込み中…