4-Chloro-2-nitrobenzaldehyde → HCID 21934721, compound

HRID 1241476Notes

Reaction equation

HRID 1241476 reaction equation
[CH3:1][Li].[Cl:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[C:6]([N+:12]([O-:14])=[O:13])[CH:5]=1>O1CCCC1>[Cl:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]([OH:9])[CH3:1])=[C:6]([N+:12]([O-:14])=[O:13])[CH:5]=1

Participants

4

Reactant 2

HCID 796744-Chloro-2-nitrobenzaldehydeHCID 178418348HCID 178418348, compound

Product 1

HCID 21934721HCID 21934721, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl lithium (46 mL, 1.4 M in Et2O), was slowly added under argon, at −78° C., to a stirred solution of 4-chloro-2-nitrobenzaldehyde (10 g, 53.9 mmol) in dry tetrahydrofuran (150 mL). After 20 min. at −78° C., the reaction mixture was quenched with water (400 mL), extracted twice with ethyl acetate (500 mL), dried (Na2SO4), and concentrated to dryness under reduced pressure. Chromatography on silica (EtOAc/CH2Cl2/EtOH, 1:6:1) yielded the title compound (7.2 g, 66%) as yellow oil: 1H NMR (400 MHz, CDCl3) δ 1.56 (d, J=6.4 Hz, 3H, ArH), 2.40 (br s, 1H, OH), 5.42 (q, J=6.4 Hz, 1H, CH), 7.63 (dd, J=8.4 Hz, J=2.0 Hz, 1H, ArH), 7.82 (d, J=8.4 Hz, 1H, ArH), 7.92 (d, J=2.0 Hz, 1H, ArH).

Workup

  1. customthe reaction mixture was quenched with water (400 mL)
  2. extractionextracted twice with ethyl acetate (500 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-ecc3b138ebab44ce9a62334acae0be1c
Source dataset
uspto-grants-2006_10
Patent number
US07115598B2

Reaction notes

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