1,3-Dinitrobenzene → 3-Fluoro-1-trifluoroacetoxyadamantane

HRID 259218

反応式

HRID 259218 の反応式
[F:1][C:2]([F:17])([F:16])[C:3]([O:5][C:6]12[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:14][CH:8]([CH2:9]3)[CH2:7]1)[CH2:13]2)=[O:4].[N+](C1C=CC=C([N+]([O-])=O)C=1)([O-])=O.[F:30]OC(F)(F)F>FC(Cl)(Cl)Cl>[F:30][C:10]12[CH2:11][CH:12]3[CH2:14][CH:8]([CH2:7][C:6]([O:5][C:3](=[O:4])[C:2]([F:16])([F:17])[F:1])([CH2:13]3)[CH2:15]1)[CH2:9]2

参加物

5

反応物 3

HCID 74521,3-DinitrobenzeneHCID 78989Hypofluorous acid, trifluoromethyl esterHCID 108794581-Adamantyl trifluoroacetate

生成物 1

HCID 539782943-Fluoro-1-trifluoroacetoxyadamantane収率 45.9%

試薬・触媒・溶媒 1

HCID 6389Trichlorofluoromethane溶媒

実験手順

A solution of 1-trifluoroacetoxyadamantane (1.0 g, 4.0 mmole, prepared by reacting adamantan-1-ol with trifluoroacetic anhydride in dry pyridine) in fluorotrichloromethane (10 ml), containing m-dinitrobenzene (80 mg, 0.48 mmole), was treated with trifluoromethyl hypofluorite (4.5 mmole) at -25° for 24 hours, air being recrystallization admitted to the reaction vessel during this time. The product was recovered in a similar manner to that described in Example 3 and was chromatographed on silica (100 g). Elution with chloroform:hexane (1:5) afforded unreacted starting material (152 mg), while elution with chloroform:hexane (1:4) gave liquid 3-fluoro-1-trifluoroacetoxyadamantane (489 mg) which appeared homogeneous by g.l.c. This product sublimed at 70° (bath)/1 mm Hg to give a crystalline solid m.p. 28°-32°; νmax (film) 1780 cm-1 ; PMR 1.5-2.6 (m, adamantyl protons); FMR φ* + 76.2 (s, CF3COO--) and + 133.5 (broad s) ppm.

後処理

  1. customair being recrystallization
  2. customThe product was recovered in a similar manner to that
  3. customwas chromatographed on silica (100 g)
  4. washElution with chloroform:hexane (1:5)
  5. customafforded unreacted
  6. washwhile elution with chloroform:hexane (1:4)

出典と根拠

ORDレコード
ord-f478b0e1373841798450be81f71acaf8
出典データセット
uspto-grants-1977_07
特許番号
US04036864

関連ノート

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