Water → (3-Nitro-5-(trifluoromethyl)phenyl)methanol

HRID 17054

反応式

HRID 17054 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1)[C:7](O)=[O:8])([O-:3])=[O:2].B.C1COCC1.O>C1COCC1>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:7][OH:8])[CH:10]=[C:11]([C:13]([F:14])([F:15])[F:16])[CH:12]=1)([O-:3])=[O:2]

参加物

5

反応物 3

HCID 962WaterHCID 6166023-Nitro-5-(trifluoromethyl)benzoic acidHCID 2723981Borane;tetrahydrofuran

生成物 1

HCID 18621888(3-Nitro-5-(trifluoromethyl)phenyl)methanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
60 °C

実験手順

To a solution of 3-nitro-5-(trifluoromethyl)benzoic acid (2.0 g, 8.5 mmol) in THF (100 mL) was added borane-THF (17 mL of a 1 M solution in THF, 17 mmol). The reaction was stirred at 60° C. for 24 hours and then poured into H2O (50 mL). The resultant mixture was extracted with EtOAc (100 mL) and the organic layer was washed with brine (50 mL), dried over Na2SO4, filtered, and concentrated. Purification by flash chromatography with 50% EtOAc/hexanes afforded [3-nitro-5-(trifluoromethyl)phenyl]methanol. Rf=0.35 (75% EtOAc/hexanes). 1H NMR (CDCl3, 500 MHz) 8.44 (s, 1H), 8.40 (s, 1H), 7.98 (s, 1H), 4.91 (s, 2H), 2.07 (bs, 1H).

後処理

  1. extractionThe resultant mixture was extracted with EtOAc (100 mL)
  2. washthe organic layer was washed with brine (50 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography with 50% EtOAc/hexanes

出典と根拠

ORDレコード
ord-871adde5e70a454ab25b5529dd7b5246
出典データセット
uspto-grants-2010_06
特許番号
US07737295B2

関連ノート

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