Hydrochloric Acid → HCID 11011384, compound

HRID 1857996Notes

Reaction equation

HRID 1857996 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.[F:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(Cl)Cl>[F:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:11]=[CH:12][C:3]=2[O:2][CH3:1])=[O:19])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 71192-MethoxynaphthaleneHCID 678794-Fluorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 11011384HCID 11011384, compoundYield 102.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-methoxynaphthalene (20.0 g, 120 mmol) and 4-fluorobenzoyl chloride (15 ml, 126 mmol) in methylene chloride (200 ml) was cooled in an ice bath under nitrogen and aluminum chloride (18.5 g, 129 mmol, 1.1 equiv.) was added portionwise over 10 minutes. The reaction mixture was stirred at room temperature for 3 h and then poured into 2N HCl (500 ml). The product was extracted into methylene chloride, and washed with brine, and dried over sodium sulfate. The organic layer was concentrated in vacuo to give 34.6 g of 1-(4-fluoro-benzoyl)-2-methoxynaphthalene as a solid (97% yield) which was used in the next step without further purification.

Workup

  1. extractionThe product was extracted into methylene chloride
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-5726ddea4ac8423ca00865a76857ead0
Source dataset
uspto-grants-2000_11
Patent number
US06150397

Reaction notes

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