p-Bromoacetophenone → 1-[4-(Thiophen-2-yl)phenyl]ethan-1-one

HRID 10625

Reaction equation

HRID 10625 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[S:11]1[CH:15]=[CH:14][CH:13]=[C:12]1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[S:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7466p-BromoacetophenoneHCID 10340Sodium CarbonateHCID 27339602-Thiopheneboronic acid

Product 1

HCID 40522101-[4-(Thiophen-2-yl)phenyl]ethan-1-oneYield 95.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Ex-17A: 4′-Bromoacetophenone (3.98 g, 20 mmol) was dissolved in ethylene glycol dimethyl ether and then the solution was degassed with nitrogen for 15 minutes. Tetrakis(triphenylphosphine)palladium(0) (2.31 g, 2 mmol) was added, and the solution was further degassed for 10 minutes. Thiophene-2-boronic acid (3.07 g, 24 mmol) was added followed by the addition of sodium carbonate solution (2 M, 45 mL). The mixture was stirred at reflux under nitrogen overnight. Most of the solvent was removed, and water was added to the remainder. The solid was filtered out and recrystallized from ethanol and water to give 3.85 g of the desired 4′-(thien-2-yl)acetophenone as a solid, 95% yield. 1H-NMR (CDCl3) δ 7.97 (d, J=9 Hz, 2H), 7.70 (d, J=9 Hz, 2H), 7.44 (d, J=4 Hz, 1H), 7.38 (d, J=5 Hz, 1H), 7.11–7.14 (m, 1H), 2.62 (s, 3H). HMRS (EI) calcd. for C12H10OS: 202.0452; found: 202.0454.

Workup

  1. customthe solution was degassed with nitrogen for 15 minutes
  2. customthe solution was further degassed for 10 minutes
  3. temperatureat reflux under nitrogen overnight
  4. customMost of the solvent was removed
  5. additionwater was added to the remainder
  6. filtrationThe solid was filtered out
  7. customrecrystallized from ethanol and water

Sources & evidence

ORD record
ord-98c5286fa77743c5adb9e6a08b1dd3b4
Source dataset
uspto-grants-2006_08
Patent number
US07094801B2

Linked notes

Loading…