Carbon tetrabromide → 1-hexyl-3-bromomethyl-4-methoxy-6-methyl-2(1H)-quinolinone

HRID 36050ノート

反応式

HRID 36050 の反応式
[CH2:1]([N:7]1[C:16]2[C:11](=[CH:12][C:13]([CH3:17])=[CH:14][CH:15]=2)[C:10]([O:18][CH3:19])=[C:9]([CH2:20]O)[C:8]1=[O:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C(Br)(Br)(Br)[Br:24].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[CH2:1]([N:7]1[C:16]2[C:11](=[CH:12][C:13]([CH3:17])=[CH:14][CH:15]=2)[C:10]([O:18][CH3:19])=[C:9]([CH2:20][Br:24])[C:8]1=[O:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

参加物

5

反応物 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 97964601-hexyl-3-hydroxymethyl-4-methoxy-6-methyl-2(1H)-quinolinone

生成物 1

HCID 152333491-hexyl-3-bromomethyl-4-methoxy-6-methyl-2(1H)-quinolinone

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 1 -hexyl-3-hydroxymethyl-4-methoxy-6-methyl-2(1H)-quinolinone (Example 12, 0.6 g) in methylene chloride (12 ml) containing carbon tetrabromide (1 g) was treated with triphenylphosphine (0.87 g) and stirred at ice bath temperature for 5mins and then at room temperature for hr. The reaction mixture was then evaporated under reduced pressure and the crude product was chromatographed on silica-gel (25 g). Elution with ether-hexane gave 1-hexyl-3-bromomethyl-4-methoxy-6-methyl-2(1H)-quinolinone as a white crystralline solid. That the expected product was obtained was confirmed by the spectral data: MS: m/e 365,367 (M+); NMR (CDCl3): δ4.12 (s, 3H, OCH3) 4.68 (s, 2H, CH2Br).

後処理

  1. waitat room temperature for hr
  2. customThe reaction mixture was then evaporated under reduced pressure
  3. customthe crude product was chromatographed on silica-gel (25 g)
  4. washElution with ether-hexane

出典と根拠

ORDレコード
ord-e35f842b46234311aded068b70c38c4b
出典データセット
uspto-grants-1995_05
特許番号
US05412104

反応ノート

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