Hydrochloric Acid → 1-(5-Bromo-6-methoxynaphthalen-2-yl)ethan-1-one

HRID 905356

Reaction equation

HRID 905356 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[Br:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][C:11]=1[O:20][CH3:21].Cl>ClCCCl.O>[C:5]([C:16]1[CH:17]=[CH:18][C:19]2[C:14](=[CH:13][CH:12]=[C:11]([O:20][CH3:21])[C:10]=2[Br:9])[CH:15]=1)(=[O:7])[CH3:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 728601-Bromo-2-methoxynaphthaleneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 6221781-(5-Bromo-6-methoxynaphthalen-2-yl)ethan-1-one

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 43 g of anhydrous AlCl3 and 24.6 g (0.313 mole) of acetyl chloride in 200 ml of 1,2-dichloroethane at 10° C. was cooled to 0° C. and added dropwise under stirring with a solution of 59.25 g (0.250 mole) of 1-bromo-2-methoxy-naphthalene in 150 ml of 1,2-dichloroethane. The resulting solution was stirred for 15 minutes then poured into a cold solution of 300 ml of water and 100 ml of 2 N hydrochloric acid. The organic phase was separated, washed first with 100 ml of 1 N hydrochloric acid and then with 100 ml of water, dried under vacuum and the obtained residue was crystallized from 2-butanol. Yield 68.11 g (98%).

Workup

  1. additionadded dropwise
  2. customThe organic phase was separated
  3. washwashed first with 100 ml of 1 N hydrochloric acid
  4. dry with materialwith 100 ml of water, dried under vacuum
  5. customthe obtained residue was crystallized from 2-butanol

Sources & evidence

ORD record
ord-8fa53b1a03c649588892f898ab3b7554
Source dataset
uspto-grants-1983_12
Patent number
US04423244

Linked notes

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