Acetic Acid Mixture with Hydrobromic Acid → HCID 68615328, compound

HRID 1431971Notes

Reaction equation

HRID 1431971 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]([C:15]#[C:16][CH2:17][NH:18][S:19]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)(=[O:21])=[O:20])=O)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[BrH:29].C(O)(=O)C>C(Cl)Cl>[Br:29][C:16]1[CH:15]=[C:13]([C:5]2[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=2)[N:18]([S:19]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH:17]=1

Participants

4

Reactant 2

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 131727710HCID 131727710, compound

Product 1

HCID 68615328HCID 68615328, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a stirred solution of 3-(p-toluenesulfonylamino)-1-propinyl 3,4,5-trimethoxyphenyl ketone (4.03 g, 10.0 mmol) in CH2Cl2 (40 ml), a 33% HBr/acetic acid solution (2.63 ml, 15.0 mmol) is added dropwise at 4° C. within 10 min. The reaction mixture is stirred for 1 h at 40° C. and extracted with CH2Cl2 and aqueous 1 N HCl solution. The organic layer is dried over MgSO4, the solvents evaporated, and the residue chromatographed on SiO2 with gradients of hexane/ethyl acetate (4:1 to 3:1) to yield the title compound as a greyish solid. 1H-NMR (300 MHz, CDCl3): 7.49 (d, J=2.0 Hz, 1H); 7.3-7.2; 7.2-7.1 (2m, 4H); 6.38 (s, 2H); 6.17 (d, J=2.0 Hz, 1H); 3.92 (s, 3H); 3.77 (s, 6H); 2.38 (s, 3H).

Workup

  1. extractionextracted with CH2Cl2 and aqueous 1 N HCl solution
  2. dry with materialThe organic layer is dried over MgSO4
  3. customthe solvents evaporated
  4. customthe residue chromatographed on SiO2 with gradients of hexane/ethyl acetate (4:1 to 3:1)

Sources & evidence

ORD record
ord-6a3a4e9b33fa41958bd90a206540ec7d
Source dataset
uspto-grants-2009_11
Patent number
US07612064B2

Reaction notes

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