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

HRID 1190912노트

반응식

HRID 1190912 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5fc50a1bef38428f823b5c944f2510fd
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680095B2

반응 노트

불러오는 중…