Hydrochloric Acid → HCID 23560508, compound

HRID 1175225Notes

Reaction equation

HRID 1175225 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[C:12](Cl)(=O)[C:13](Cl)=O.[Al+3].[Cl-].[Cl-].[Cl-].Cl.[OH-].[Na+]>C(Cl)Cl.CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([C:7]([C:2]2[CH:3]=[CH:4][C:12]([CH3:13])=[CH:6][CH:10]=2)=[O:9])[CH:10]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 331275-Bromo-2-chlorobenzoic acidHCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 23560508HCID 23560508, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

To a stirred suspension of compound 5-bromo-2-chlorobenzoic acid (20 g, 85.5 mmol) in 200 mL of CH2Cl2 containing oxalyl chloride (11.2 mL) was added 0.5 mL of DMF. Once the vigorous evolution of gas ceased, the reaction was stirred overnight and then the volatiles were removed under reduced pressure. After dissolving the crude 5-bromo-2-chlorobenzoyl chloride in 150 mL of toluene, the solution was cooled to −10° C. Then AlCl3 (22.4 g, 170 mmol) was added while insuring the temperature did not exceed 0° C. HCl gas emission was trapped by passing the gas over a stirred concentrated NaOH solution. HPLC-MS revealed the reaction to be 98% complete after the addition was finished. The reaction was quenched by pouring over ice. The suspension was diluted with H2O and extracted 3× with CH2Cl2. The combined organic extracts were washed 2× with 1N HCl, 1× with H2O, 2× with 1M NaOH, and 2× with brine prior to drying over Na2SO4. After removal of the volatiles, crystallization of the crude product from ethanol (80 mL) yielded intermediate AG (16 g).

Workup

  1. customthe volatiles were removed under reduced pressure
  2. dissolutionAfter dissolving the crude 5-bromo-2-chlorobenzoyl chloride in 150 mL of toluene
  3. customdid not exceed 0° C
  4. customthe reaction
  5. additioncomplete after the addition
  6. customThe reaction was quenched
  7. additionby pouring over ice
  8. additionThe suspension was diluted with H2O
  9. extractionextracted 3× with CH2Cl2
  10. washThe combined organic extracts were washed 2× with 1N HCl, 1× with H2O, 2× with 1M NaOH, and 2× with brine
  11. dry with materialto drying over Na2SO4
  12. customAfter removal of the volatiles, crystallization of the crude product from ethanol (80 mL)
  13. customyielded intermediate AG (16 g)

Sources & evidence

ORD record
ord-78436e90cf2e4ac5b36b63e46ead5f70
Source dataset
uspto-grants-2010_11
Patent number
US07838499B2

Reaction notes

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