Methanol → (3-Bromo-5-nitrophenyl)methanol

HRID 391450

反応式

HRID 391450 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:5](O)=[O:6].O1CCCC1.B.CO>O1CCCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1

参加物

6

反応物 3

HCID 887MethanolHCID 2393363-Bromo-5-nitrobenzoic acidHCID 2723981Borane;tetrahydrofuran

生成物 1

HCID 14866972(3-Bromo-5-nitrophenyl)methanol

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

3-Bromo-5-nitrobenzoic acid (3.2 g, 13.0 mmol) was suspended in tetrahydrofuran (25 mL) and cooled to 0° C. To this solution was added borane tetrahydrofuran complex (1 M in tetrahydrofuran, 26 mL, 26 mmol) cautiously over 15 min. The reaction mixture was allowed to warm to room temperature overnight. The mixture was cooled to 0° C., treated with excess methanol, diluted with ethyl acetate, washed with 1 N sodium hydroxide (2×), then brine (2×), dried over sodium sulfate, and concentrated to afford 3.0 g (99%) as a white powder. 1H-NMR (CDCl3, 300 MHz) 8.24 (s, 1H), 8.13 (s, 1H), 7.82 (s, 1H), 4.78 (s, 2H). Mass spec.: 233.88 (MH)+.

後処理

  1. temperatureto warm to room temperature overnight
  2. temperatureThe mixture was cooled to 0° C.
  3. washwashed with 1 N sodium hydroxide (2×)
  4. dry with materialbrine (2×), dried over sodium sulfate
  5. concentrationconcentrated
  6. customto afford 3.0 g (99%) as a white powder

出典と根拠

ORDレコード
ord-1ab653f2233a42e5b073c8f28583978c
出典データセット
uspto-grants-2013_02
特許番号
US08383821B2

関連ノート

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