Benzyl Bromide → 1-Benzyl-5-chloro-1H-indole

HRID 5596

反応式

HRID 5596 の反応式
C1OCCOCCOCCOCCOCCOC1.CC(C)([O-])C.[K+].[Cl:25][C:26]1[CH:27]=[C:28]2[C:32](=[CH:33][CH:34]=1)[NH:31][CH:30]=[CH:29]2.[CH2:35](Br)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>CCOCC.O>[CH2:35]([N:31]1[C:32]2[C:28](=[CH:27][C:26]([Cl:25])=[CH:34][CH:33]=2)[CH:29]=[CH:30]1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

参加物

7

反応物 4

HCID 7498Benzyl BromideHCID 2855718-Crown-6HCID 871105-ChloroindoleHCID 23665647Potassium tert-butoxide

生成物 1

HCID 184763621-Benzyl-5-chloro-1H-indole収率 90%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒2 回

実験手順

To a solution of 0.8 g (3.03 mmoles) of 18-crown-6 in 100 mL of dry ether was added 4.39 g (39.12 mmoles) potassium tert-butoxide. The mixture was stirred while 5.08 g (33.51 mmoles) of 5-chloroindole was added. The stirring was continued for 0.5 hour. Most of the solid dissolved. Then 6.69 g (39.11 mmoles) of benzyl bromide in 40 mL of ether was added during 0.5 hours. The stirring was continued for 27 hours. Water (100 mL) was added. The layers were separated. The aqueous layer was extracted with ether (2×75 mL). The combined ether phases were washed with 50 mL of brine and dried over MgSO4. Evaporation of the solvent left 9.17 g of orange oil. The oil was chromatographed on a 700 g column of silica gel. The column was eluted with 1:2 CH2Cl2 -Skellysolve B and 200 mL fractions were collected. The fractions were assayed by silica gel tlc (2×8") (1:2 CH2Cl2 -Skellysolve B). Fractions 10-14 were combined giving 7.26 g (90%) of 1-benzyl-5-chloroindole as a yellow oil.

後処理

  1. additionwas added
  2. dissolutionMost of the solid dissolved
  3. waitThe stirring was continued for 27 hours
  4. customThe layers were separated
  5. extractionThe aqueous layer was extracted with ether (2×75 mL)
  6. washThe combined ether phases were washed with 50 mL of brine
  7. dry with materialdried over MgSO4
  8. customEvaporation of the solvent
  9. waitleft 9.17 g of orange oil
  10. customThe oil was chromatographed on a 700 g column of silica gel
  11. washThe column was eluted with 1:2 CH2Cl2 -Skellysolve B and 200 mL fractions
  12. customwere collected

出典と根拠

ORDレコード
ord-0121012381ad40bb9bdeb58d7a76e8eb
出典データセット
uspto-grants-1993_09
特許番号
US05245046

関連ノート

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