Acetic Acid Mixture with Hydrobromic Acid → 2-Bromo-4-(4-chlorophenyl)-1,3-thiazole

HRID 1830864Notes

Reaction equation

HRID 1830864 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([S:11][C:12]#[N:13])=O)=[CH:4][CH:3]=1.[BrH:14].C(O)(=O)C>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([Br:14])[S:11][CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 22049674HCID 22049674, compound

Product 1

HCID 220497472-Bromo-4-(4-chlorophenyl)-1,3-thiazoleYield 44%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

The compound (40) (2.1 g, 10.0 mmol) was suspended in acetic acid (10 ml) and 47% HBr-acetic acid (1 ml) was added. The mixture was stirred with heating at 80° C. for 2 hrs. The reaction mixture was concentrated under reduced pressure to dryness and the residue was partitioned between ethyl acetate and 5% NaHCO3 aq. The aqueous layer was extracted with ethyl acetate, and the extracts were combined, washed with saturated brine and dried (MgSO4). The solvent was evaporated under reduced pressure and isopropyl ether was added to the obtained residue, which was filtrated to give the title compound (1.2 g, 44%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure to dryness
  2. customthe residue was partitioned between ethyl acetate and 5% NaHCO3 aq. The aqueous layer
  3. extractionwas extracted with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried (MgSO4)
  6. customThe solvent was evaporated under reduced pressure and isopropyl ether
  7. additionwas added to the obtained residue, which
  8. filtrationwas filtrated

Sources & evidence

ORD record
ord-8e303cfd1dd74d4da8d9b66468031a15
Source dataset
uspto-grants-2006_06
Patent number
US07067537B2

Reaction notes

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