Hydrochloric Acid → HCID 15278484, compound

HRID 617699Notes

Reaction equation

HRID 617699 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:12])[CH2:9][CH2:10][S:11][C:6]=2[C:5]([Cl:13])=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[Br:18]Br.Cl>C(Cl)Cl>[Br:18][C:3]1[CH:4]=[C:5]([Cl:13])[C:6]2[S:11][CH2:10][CH2:9][C:8](=[O:12])[C:7]=2[C:2]=1[Cl:1]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24408BromineHCID 6451240Aluminum(III) ChlorideHCID 13953738HCID 13953738, compound

Product 1

HCID 15278484HCID 15278484, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 45.18 g (0.19 mol) of the title compound of Step B in 400 mL of methylene chloride was added dropwise at room temperature under nitrogen to a mixture of 64.6 g (0.48 mol) of aluminum chloride in 400 mL of methylene chloride. After stirring for 15 min, 10.5 mL (0.20 mol) of bromine was added dropwise and the mixture was refluxed for 10 min. The mixture, while still warm, was poured into 550 g of ice containing 110 mL of concentrated hydrochloric acid, and the resulting mixture was extracted with diethyl ether (2×500 mL). The combined organic layers were dried (Na2SO4), filtered, and evaporated to dryness to yield 57.37 g of the title compound of Step C as a solid melting at 89-90° C. 1H NMR (CDCl3): δ3.0 (m,2H), 3.3 (m,2H), 7.7 (s,1H).

Workup

  1. temperaturethe mixture was refluxed for 10 min
  2. temperatureThe mixture, while still warm
  3. extractionthe resulting mixture was extracted with diethyl ether (2×500 mL)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-59c5c41426384917a5e4c09377c5bd2c
Source dataset
uspto-grants-1999_09
Patent number
US05952266

Reaction notes

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