Toluene → 3-Fluoro-4-phenylmethoxyaniline

HRID 455830ノート

反応式

HRID 455830 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:10]=1[F:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.C([O-])=O.[NH4+]>[Fe].O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][C:10]=1[F:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 1140TolueneHCID 2723923Ammonium formateHCID 220309121-(Benzyloxy)-2-fluoro-4-nitrobenzene

生成物 1

HCID 219518923-Fluoro-4-phenylmethoxyaniline収率 87.2%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 962Water溶媒

実験手順

A mixture of 1-benzyloxy-2-fluoro-4-nitro-benzene (44 g, 178 mmol), toluene (400 ml), ammonium formate (35 g), iron (30 g), and water (400 ml) was heated to reflux with stirring overnight. The reaction mixture was filtered through celite and washed with ethyl acetate (400 ml). The organic layer was separated and washed with brine (300 ml), dried over sodium sulfate and concentrated to give 4-benzyloxy-3-fluoro-phenylamine as an oil (33.7 g, 87%). 1H NMR (400 MHz, CDCl3): δ 7.41-7.29 (m, 5H), 6.79 (t, 1H), 6.45 (dd, 1H), 6.14 (dd, 1H), 5.02 (s, 2H), 3.50 (s, 2H). LC/MS: (M+1) 218.

後処理

  1. temperaturewas heated
  2. temperatureto reflux
  3. filtrationThe reaction mixture was filtered through celite
  4. washwashed with ethyl acetate (400 ml)
  5. customThe organic layer was separated
  6. washwashed with brine (300 ml)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-e1772f5d88de4a74a9fa6219457b3ee5
出典データセット
uspto-grants-2013_07
特許番号
US08497284B2

反応ノート

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