Dichloromethane → HCID 68485519, compound

HRID 1959148Notes

Reaction equation

HRID 1959148 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[CH3:11][O:12][C:13]1[CH:14]=[C:15](C)[CH:16]=[C:17]([O:19][CH3:20])[CH:18]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl[CH2:27]Cl>>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([C:14]2([CH3:27])[CH:15]=[CH:16][C:17]([O:19][CH3:20])=[CH:18][CH:13]2[O:12][CH3:11])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 678794-Fluorobenzoyl chlorideHCID 778443,5-DimethoxytolueneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 68485519HCID 68485519, compound

Conditions

Temperature
-40 °C

Procedure

4-Fluorobenzoyl chloride (7.76 mL) was added to a solution of 3,5-dimethoxytoluene (10 g) in dichloromethane (200 mL) and aluminum chloride (13.7 g) was added to the solution cooled at −40° C. and the mixture was stirred at the same temperature for 30 minutes. The reaction mixture was poured into ice water and the mixture was extracted with dichloromethane (200 mL×3). The combined organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel (Solvent; petroleum ether/ethyl acetate=50/1) to give the titled compound (7.5 g) as a yellow powder.

Workup

  1. additionwas added to the solution
  2. extractionthe mixture was extracted with dichloromethane (200 mL×3)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel (Solvent; petroleum ether/ethyl acetate=50/1)

Sources & evidence

ORD record
ord-5855b871ce0b4e9c89db218299eda835
Source dataset
uspto-grants-2013_04
Patent number
US08410166B2

Reaction notes

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