Carbon Dioxide → 5-Bromo-2-chlorobenzoyl chloride

HRID 2080538Notes

Reaction equation

HRID 2080538 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4](O)=[O:5].C(Cl)(=O)C([Cl:15])=O.Cl.C(=O)=O>C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4]([Cl:15])=[O:5]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 331275-Bromo-2-chlorobenzoic acidHCID 65578Oxalyl chloride

Product 1

HCID 27568715-Bromo-2-chlorobenzoyl chlorideYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

8.00 kg 2-chloro-5-bromobenzoic acid was suspended in 80.00 L methylene chloride (KF of methylene chloride<0.1% H2O) and 0.02 L of DMF added at 20° C. 5.18 Kg oxalyl chloride were slowly added and the internal temperature maintained below 25° C. The addition was slightly exothermic; gas evolution of HCl and CO2 occurred. The reaction was run at 20-25° C. overnight; a clear solution was obtained. The mixture was concentrated in vacuum to an oily residue and degased at 40° C. in vacuum. Yield of 2-chloro-5-bromobenzoic acid chloride: 8.63 kg (33.98 mol, yield 100.0%)

Workup

  1. temperaturethe internal temperature maintained below 25° C
  2. additionThe addition
  3. customa clear solution was obtained
  4. concentrationThe mixture was concentrated in vacuum to an oily residue
  5. customdegased at 40° C. in vacuum

Sources & evidence

ORD record
ord-63a94d36a6364c9082e3382603d6126e
Source dataset
uspto-grants-2011_04
Patent number
US07932379B2

Reaction notes

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