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

HRID 1190912Notes

Reaction equation

HRID 1190912 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-5fc50a1bef38428f823b5c944f2510fd
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

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