Hydrochloric Acid → (2-Fluoro-5-nitrophenyl)methanol

HRID 1190912ノート

反応式

HRID 1190912 の反応式
[F:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH:4]=[O:5].[BH4-].[Na+].Cl>CO>[F:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH2:4][OH:5]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 27347702-Fluoro-5-nitrobenzaldehydeHCID 4311764Sodium borohydride

生成物 1

HCID 4437169(2-Fluoro-5-nitrophenyl)methanol

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

To a solution of 2-fluoro-5-nitro-benzaldehyde (1000 mg, 5.91 mmoles) in MeOH (10 mL) was added NaBH4 (182 mg, 4.82 mmoles). The reaction mixture was stirred for 3 h at 0° C. The reaction mixture was acidified with HCl 1M until pH4, concentrated. 50 mL of water was added and the compound was extracted with Et2O. The organic layer was dried over MgSO4, filtered, evaporated. Expected compound was obtained as a pale yellow solid (1007 mg, 99% yield). mp=62-64° C. 1H NMR (300 MHz, CDCl3) δ8.43; (dd, 6-CH, J=6.2 Hz and 2.9 Hz, 1H), 8.19; (ddd, J=9 Hz, 4.5 Hz and 2.9 Hz, 1H), 7.20; (dd, J=9.0 Hz and 9.0 Hz, 1H), 4.85; (d, J=3.6 Hz, 2H), 2.12; (s large, 1H). 13C NMR (75 MHz, CDCl3) δ125.0; (CH, d, J=10.0 Hz), 124.7; (CH, d, J=6.9 Hz), 116.2; (CH, d, J=23.6 Hz), 58.2; (CH2).

後処理

  1. concentrationconcentrated
  2. addition50 mL of water was added
  3. extractionthe compound was extracted with Et2O
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated

出典と根拠

ORDレコード
ord-5fc50a1bef38428f823b5c944f2510fd
出典データセット
uspto-grants-2014_03
特許番号
US08680095B2

反応ノート

読み込み中…