ChemicalBook CAS DataBase List 2-CHLORO-6-NITROBENZALDEHYDE

2-CHLORO-6-NITROBENZALDEHYDE synthesis

7synthesis methods

Product Name:2-CHLORO-6-NITROBENZALDEHYDE
CAS Number:6361-22-4
Molecular formula:C7H4ClNO3
Molecular Weight:185.56

83-42-1 Synthesis

83-42-1
270 suppliers
$9.00/5g

4637-24-5 Synthesis

4637-24-5
610 suppliers
$5.00/25g

6361-22-4
134 suppliers
$17.00/250mg

Yield: 86%

Reaction Conditions:

Stage #1:6-chloro-2-nitrotoluene;N,N-dimethyl-formamide dimethyl acetal in N,N-dimethyl-formamide at 140; for 16 h;
Stage #2: with sodium periodate in water;N,N-dimethyl-formamide at 0 - 20; for 9 h;

Steps:

109
Example 109; This example concerns the synthesis of Aldehyde 4: To a stirred solution of1 (18.53 g, 108.0 mmol) in dry DMF (240 mL) was added N,JV-dimethylformamide dimethyl acetal (DMF'DMA) (39.5 g, 44.0 mL, 331 mmol). After heating at 140°C for 16 h, the dark red solution was cooled to 0°C and added slowly, over 1 h via cannula, to a rapidly stirred solution OfNaIO₄ (83.0 g, 388.0 mmol) in H₂O (291 mL) and DMF (77 mL) at 0°C. The reaction flask was washed with DMF (20 mL) at 0°C and added to NaIO₄ mixture. The reaction was stirred at 0°C for 2 h then allowed to warm to rt. After an additional 6 h, the orange solution was filtered and rinsed with PhMe/EtOAc (1 : 1 , 200 mL). The filtrate was then washed with H₂O (3 x 150 mL) and sat. aq. NaCl (3 x 150 mL). The dried (MgSO₄) extract was concentrated in vacuo to a dark red oil, and hexanes (40 mL) were added. Solids were isolated and recrystalized in PhMe to give the known aldehyde 4 (17.23 g, 92.88 mmol, 86%). ¹H NMR (400 MHz, CDCl₃) δ 10.42 (s, IH), 8.01 (dd, J= 1.0, 8.2 Hz, IH), 7.79 (dd, J= 1.0, 8.1 Hz₅ IH), 7.65 (t, J= 8.1 Hz, IH); ¹³C NMR (100 MHz, CDCl₃) δ 188.6, 148.4, 138.6, 132.9, 132.4, 123.4, 121.9.

References:

STATE OF OREGON ACTING BY AND THROUGH THE STATE BOARD OF HIGHER EDUCATION ON BEHALF OF OREGON STATE UNIVERSITY WO2008/156656, 2008, A2 Location in patent:Page/Page column 46; 177

83-42-1 Synthesis

83-42-1
270 suppliers
$9.00/5g

6361-22-4
134 suppliers
$17.00/250mg

References

50907-57-8 Synthesis