Phenacyl bromide → HCID 54681232, compound

HRID 613113Notes

Reaction equation

HRID 613113 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:5][C:4](=[O:14])[C:3]=1[SH:15].C(N(CC)CC)C.Br[CH2:24][C:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:26]>C(Cl)Cl>[OH:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:5][C:4](=[O:14])[C:3]=1[S:15][CH2:24][C:25](=[O:26])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 8471TriethylamineHCID 54681459HCID 54681459, compound

Product 1

HCID 54681232HCID 54681232, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-hydroxy-3-mercapto-6-phenyl-2-pyrone (0.175, 0.840 mmol, prepared as in R. F. Harris, J. E. Dunbar, U.S. Pat. No. 3,818,046) in CH2Cl2 (3.0 mL) under an N2 atmosphere was treated with triethylamine (0.12 mL, 0.84 mmol) followed by bromoacetophenone (0.167 g, 0.840 mmol). The mixture was allowed to stir for 30 min. at ambient temperature then the solvent removed in vacuo. The residue was then diluted with diethyl ether and extracted with saturated Na2CO3 (3×50 mL). The aquous layers were then combined, acidifed with conc. HCl, and extracted with CH2Cl2 (3×100 mL). The organic layers were combined, dried with Na2SO4, and the solvent removed in vacuo to give the title compound (0.066 g, m.p. 164 -166 ° C.) which was dried in vacuo. 1H NMR (300 MHz, CDCl3) δ9.900 (bs, 1 H), 7.970 (d, 2 H, J=7.1 Hz), 7.810 (d, 2 H, J=8 Hz), 7.615 (t, 1 H, J =4 Hz), 7.505-7.443 (m, 5 H), 6.619 (s, 1 H), 4.334 (s, 2 H).

Workup

  1. customthe solvent removed in vacuo
  2. additionThe residue was then diluted with diethyl ether
  3. extractionextracted with saturated Na2CO3 (3×50 mL)
  4. extractionextracted with CH2Cl2 (3×100 mL)
  5. dry with materialdried with Na2SO4
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-67992bc73aea40a1a5e18cbd0dc15307
Source dataset
uspto-grants-1999_12
Patent number
US06005103

Reaction notes

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