Hydrochloric Acid → HCID 21915324, compound

HRID 1246552Notes

Reaction equation

HRID 1246552 reaction equation
[Br:1][C:2]1[CH:6]=[CH:5][S:4][CH:3]=1.[CH3:7][O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](Cl)=[O:14])=[CH:11][CH:10]=1.Cl.O>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:13]([C:12]1[CH:16]=[CH:17][C:9]([O:8][CH3:7])=[CH:10][CH:11]=1)=[O:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 7477p-Anisoyl chlorideHCID 133833-Bromothiophene

Product 1

HCID 21915324HCID 21915324, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent3×

Procedure

Treat a stirred, chilled (0° C.) solution of 3-bromothiophene (20 g, 0.123 mol) and dichloromethane (150 mL) with titanium tetrachloride in dichloromethane (184 mL, 1.0M) at such a rate as to maintain the temperature below 5° C. Add dropwise a solution of 4-methoxybenzoyl chloride (20.9 g, 0.123 mol) and dichloromethane (75 mL) at such a rate as to maintain the temperature below 5° C. Stir one hour at 0–5° C., then quench the reaction by addition of ice (100 mL) and 6N hydrochloric acid at such a rate that the internal temperature remains at or below 10° C. Add more water (100 mL), separate the organic phase, wash with water, dry (Na2SO4), filter and evaporate to an oil which solidifies. Recrystallize the solid from ether to afford the title compound as off-white crystals (19.7 g, 54%).

Workup

  1. additionTreat a stirred
  2. temperatureto maintain the temperature below 5° C
  3. temperatureto maintain the temperature below 5° C
  4. customquench
  5. customthe reaction
  6. custombelow 10° C
  7. customseparate the organic phase
  8. washwash with water
  9. dry with materialdry (Na2SO4)
  10. filtrationfilter
  11. customevaporate to an oil which
  12. customRecrystallize the solid from ether

Sources & evidence

ORD record
ord-1c6aaa85b2414cd4b0d4389837938236
Source dataset
uspto-grants-2006_10
Patent number
US07125903B1

Reaction notes

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