Potassium Carbonate → 6-bromohexyl (2Z)-4-(acetyloxy)-3-[4-(methylsulfonyl)phenyl]-2-phenylbut-2-enoate

HRID 1375707Notes

Reaction equation

HRID 1375707 reaction equation
[C:1]([O:4][CH2:5]/[C:6](/[C:17]1[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=1)=[C:7](/[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)\[C:8]([OH:10])=[O:9])(=[O:3])[CH3:2].[Br:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]Br.C([O-])([O-])=O.[K+].[K+].[Cl-].[NH4+]>CN(C=O)C>[C:1]([O:4][CH2:5]/[C:6](/[C:17]1[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=1)=[C:7](/[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)\[C:8]([O:10][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][Br:27])=[O:9])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 123681,6-DibromohexaneHCID 25517Ammonium ChlorideHCID 11617716(Z)-4-Acetoxy-3-(4-(methylsulfonyl) phenyl)-2-phenylbut-2-enoic acid

Product 1

HCID 115701256-bromohexyl (2Z)-4-(acetyloxy)-3-[4-(methylsulfonyl)phenyl]-2-phenylbut-2-enoateYield 96.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2.6 g of (2Z)-4-(acetyloxy)-3-[4-(methylsulfonyl)phenyl]-2-phenylbut-2-enoic acid and 17 g of 1,6-dibromohexane in 30 mL of DMF was stirred at rt with 1.0 g K2CO3 for 1 hr. Then saturated ammonium chloride solution was added and extracted with EtOAc. The organic layer was combined and washed with brine and dried over Na2SO4. The solvent was evaporated and the residue was purified by flash chromatography over silica gel (5–50% EtOAc/hexane) to afford 3.6 g of the titled compound as a white solid. 1H NMR (acetone-d6, 500 M Hz): δ 7.80 (d, 2H), 7.47 (d, 2H), 7.22–7.15 (m, 3H), 7.12–7.05 (m, 2H), 5.21 (s, 2H), 4.27 (t, 2 H), 3.48 (t, 2 H), 3.08 (s, 3H), 1.93 (s, 3H), 1.86–1.80 (m, 2H), 1.74–1.68 (m, 2H), 1.50-1.41 (m, 2H), 1.41-1.34(m, 2H).

Workup

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. customThe solvent was evaporated
  5. customthe residue was purified by flash chromatography over silica gel (5–50% EtOAc/hexane)

Sources & evidence

ORD record
ord-bd09989f0e074b14ae59eaafb8e52b61
Source dataset
uspto-grants-2007_01
Patent number
US07169809B2

Reaction notes

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