4-Nitrobenzoyl chloride → 4-Nitrobenzaldehyde

HRID 1777083Notes

Reaction equation

HRID 1777083 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[N+:5]([C:8]1[CH:16]=[CH:15][C:11]([C:12](Cl)=[O:13])=[CH:10][CH:9]=1)([O-:7])=[O:6].CC1N=C(CC2C3C(C=CC=CC=3)=CC=2C)SC=1>ClC(Cl)C>[N+:5]([C:8]1[CH:9]=[CH:10][C:11]([CH:12]=[O:13])=[CH:15][CH:16]=1)([O-:7])=[O:6]

Participants

5

Reactant 3

HCID 85024-Nitrobenzoyl chlorideHCID 6451240Aluminum(III) Chloride2×HCID 86718317HCID 86718317, compound

Product 1

HCID 5414-Nitrobenzaldehyde

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

AlCl3 (101 mg, 0.757 mmol) was weighed quickly into an argon-flushed vial. While the vial was being purged with argon, dichloroethane was added slowly. The ensuing mixture was syringed quickly into a round-bottom flask and cooled to 0° C. A solution of 4-nitro benzoyl chloride (70 mg, 0.377 mmol) in dichloroethane was added slowly into the suspension of AlCl3 at O—C. This mixture was stirred at 0° C. for 30 min after which a fresh solution of compound 6 (64 mg, 0.253 mmol) in dichloroethane was added slowly to the reaction mixture being stirred at 0° C. After the reaction was stirred at 0° C. for 30 min, it was brought to room temperature and then stirred for another 30 min. The reaction was quenched by adding ice-cold water slowly. The organic layer was extracted into dichloromethane and washed with water and brine, dried with MgSO4 and purified using flash chromatography (ethyl acetate and hexane). The purified material was dried down into a brown/orange solid. Yield: 45 mg, 44%. 1H NMR (400 MHz, CDCl3) δ 8.63 (d, J=9.84 Hz, 1H), 8.44 (d, J=9.89 Hz, 1H), 8.29 (d, J=8.82 Hz, 2H), 7.86 (d, J=8.81 Hz, 2H), 7.71 (t, J=9.82 Hz, 1H), 7.46 (t, J=9.72 Hz, 1H), 7.29 (t, J=9.93 Hz, 1H), 6.67 (s, 1H), 4.70 (s, 2H), 2.42 (s, 3H), 2.39 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 192.2, 170.3, 152.3, 150.4, 149.5, 146.3, 141.4, 140.2, 138.2, 135.6, 133.7, 130.2, 127.2, 125.0, 124.3, 123.6, 123.3, 113.2, 29.0, 16.9. HRMS (ES) calcd MH+ [C23H19N2O3S]+403.1038. found 403.1106.

Workup

  1. customflushed vial
  2. customWhile the vial was being purged with argon, dichloroethane
  3. additionwas added slowly
  4. customThe ensuing mixture was syringed quickly into a round-bottom flask
  5. additionwas added slowly to the reaction mixture
  6. stirringAfter the reaction was stirred at 0° C. for 30 min
  7. customwas brought to room temperature
  8. stirringstirred for another 30 min
  9. customThe reaction was quenched
  10. additionby adding ice-cold water slowly
  11. extractionThe organic layer was extracted into dichloromethane
  12. washwashed with water and brine
  13. dry with materialdried with MgSO4
  14. custompurified
  15. customThe purified material was dried down into a brown/orange solid

Sources & evidence

ORD record
ord-544420ff801c426d99ce09b90b1b2318
Source dataset
uspto-grants-2016_02
Patent number
US09266847B2

Reaction notes

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