5-Chloro-2-nitrobenzaldehyde → (5-Chloro-2-nitro-phenyl)-(6-chloro-pyridin-3-yl)-methanol

HRID 495530Notes

Reaction equation

HRID 495530 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][N:3]=1.[N+:9]([C:12]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:13]=1[CH:14]=[O:15])([O-:11])=[O:10]>C1COCC1>[Cl:20][C:17]1[CH:18]=[CH:19][C:12]([N+:9]([O-:11])=[O:10])=[C:13]([CH:14]([C:5]2[CH:4]=[N:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[OH:15])[CH:16]=1

Participants

4

Reactant 2

HCID 811235-Chloro-2-nitrobenzaldehydeHCID 43971762-Chloro-5-iodopyridine

Product 1

HCID 22327314(5-Chloro-2-nitro-phenyl)-(6-chloro-pyridin-3-yl)-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-45 °C

Procedure

A solution of 1.0 g 2-chloro-5-iodopyridine (4.1 mmol, 1.0 eq.) in 10 mL anhyd. THF was stirred at −40° C. to −50° C. After five minutes, 2.2 mL of 2.1 MiPrMgBr/THF (4.6 mmol, 1.1 eq.) were added drop wise over 1 minute and the reaction mixture is maintained at −40 to −50° C. for 30 minutes. 1.3 g 2-nitro-5-chlorobenzaldehyde (7.0 mmol, 1.7 eq.) was then added and the reaction was maintained at −50° C. After 1 hour, the reaction was allowed to warm to −10° C., and quenched with 50 mL saturated brine after a further fifteen minutes. The crude product was extracted with EtOAc, dried on Na2SO4 and concentrated by rotary evaporation to yield desired product. MS: (M+H)/z=298.9

Workup

  1. temperaturethe reaction was maintained at −50° C
  2. waitAfter 1 hour
  3. temperatureto warm to −10° C.
  4. customquenched with 50 mL saturated brine after a further fifteen minutes
  5. extractionThe crude product was extracted with EtOAc
  6. customdried on Na2SO4
  7. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-9816f11b26b84e26ad352a72044866e8
Source dataset
uspto-grants-2005_09
Patent number
US06939885B2

Reaction notes

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