6-Acetyltetralin → 2-Bromo-1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethan-1-one

HRID 1401758Notes

Reaction equation

HRID 1401758 reaction equation
[CH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[C:11](=[O:13])[CH3:12].[Br-:14].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1>C1COCC1>[Br:14][CH2:12][C:11]([C:2]1[CH:3]=[CH:4][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[CH:1]=1)=[O:13]

Participants

4

Reactant 2

HCID 698856-AcetyltetralinHCID 17977687Phenyltrimethylammonium bromide dibromide

Product 1

HCID 73539912-Bromo-1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

25 g (143 mmol) of 1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethanone were dissolved in 750 ml of THF, 64.7 g (172 mmol) of phenyltrimethylammonium tribromide were added, and the mixture was stirred at room temperature for 15 h. The resultant precipitate was filtered, and the filtrate was evaporated to dryness. The residue was taken up in ethyl acetate, washed with 2× sat. sodium hydrogencarbonate solution and 1× sat. sodium chloride solution, the organic phase was dried over sodium sulfate and evaporated to dryness.

Workup

  1. filtrationThe resultant precipitate was filtered
  2. customthe filtrate was evaporated to dryness
  3. washwashed with 2× sat. sodium hydrogencarbonate solution and 1× sat. sodium chloride solution
  4. dry with materialthe organic phase was dried over sodium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-5f41ff47bdd540c48eaa6c86f10ca94c
Source dataset
uspto-grants-2014_12
Patent number
US08907098B2

Reaction notes

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