Trimethylaluminum → 6-Bromo-2-(2,2,2-trifluoro-1,1-dimethylethyl)quinoline

HRID 1094659

反応式

HRID 1094659 の反応式
CS(O[C:6]([C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([Br:22])[CH:18]=2)[N:13]=1)([CH3:11])[C:7]([F:10])([F:9])[F:8])(=O)=O.[CH3:23][Al](C)C>C1CCCCC1>[Br:22][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]([C:6]([CH3:23])([CH3:11])[C:7]([F:10])([F:9])[F:8])[CH:21]=[CH:20]2

参加物

4

反応物 2

HCID 16682925TrimethylaluminumHCID 574581676-Bromoquinolin-2-yl-2,2,2-trifluoro-1-methylethyl methanesulfonate

生成物 1

HCID 574581686-Bromo-2-(2,2,2-trifluoro-1,1-dimethylethyl)quinoline収率 100.2%

試薬・触媒・溶媒 1

HCID 8078Cyclohexane溶媒

実験手順

A suspension of 6-bromoquinolin-2-yl-2,2,2-trifluoro-1-methylethyl methanesulfonate (11.97 g, 30 mmol) in cyclohexane (120 ml) was added trimethylaluminum (120 ml, 123 mmol, 1.03M in hexane solution) at room temperature, and the mixture was stirred at room temperature for 1 hour. The reaction was carefully quenched with saturated sodium bicarbonate aqueous solution (30 ml), brine (10 ml) and diluted with ethyl acetate and heptane (200 ml). After the mixture was stirred for 30 minutes, formed precipitate was removed by celite and washed with ethyl acetate. The filtrate was concentrated and purified through silica gel column chromatography eluting with hexane only to furnish the title compound (9.56 g, 80% yield) as colorless oil. 1H NMR (300 MHz, CDCl3) ppm 1.72 (6H, s), 7.66 (1H, d, J=8.8 Hz), 7.75-7.80 (1H, m), 7.96-8.00 (2H, m), 8.06 (1H, d, J=8.8 Hz). MS (ESI): m/z 318, 320 (M+H)+.

後処理

  1. customThe reaction was carefully quenched with saturated sodium bicarbonate aqueous solution (30 ml), brine (10 ml)
  2. additiondiluted with ethyl acetate and heptane (200 ml)
  3. stirringAfter the mixture was stirred for 30 minutes
  4. customformed precipitate
  5. customwas removed by celite
  6. washwashed with ethyl acetate
  7. concentrationThe filtrate was concentrated
  8. custompurified through silica gel column chromatography
  9. washeluting with hexane only

出典と根拠

ORDレコード
ord-44f7ef7c10ab4950ac7a9f7ec3423e9d
出典データセット
uspto-grants-2012_03
特許番号
US08134004B2

関連ノート

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