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

HRID 1190912Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1190912
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-5fc50a1bef38428f823b5c944f2510fd
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680095B2

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