1-Naphthalen-1-ylpropan-1-one → 2-Bromo-1'-propionaphthone

HRID 33557Notes

Reaction equation

HRID 33557 reaction equation
[C:1]1([C:11](=[O:14])[CH2:12][CH3:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Br-:15].[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>O1CCCC1>[Br:15][CH:12]([CH3:13])[C:11]([C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)=[O:14]

Participants

4

Reactant 2

HCID 2311591-Naphthalen-1-ylpropan-1-oneHCID 17977687Phenyltrimethylammonium bromide dibromide

Product 1

HCID 2311612-Bromo-1'-propionaphthoneYield 175.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(naphth-1-yl)-1-propanone (4.0 g) in anhydrous tetrahydrofuran (50 ml) was added phenyltrimethylammonium tribromide (8.0 g). The resulting mixture was stirred overnight at room temperature then partitioned between petroleum ether and aqueous sodium carbonate solution. The organic layer was separated, washed with water, brine, dried with sodium sulphate, filtered and evaporated in vacuo to yield crude 2-bromo-1-(naphth-1-yl)-1-propanone (5.7 g).

Workup

  1. customthen partitioned between petroleum ether and aqueous sodium carbonate solution
  2. customThe organic layer was separated
  3. washwashed with water, brine
  4. dry with materialdried with sodium sulphate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-6f9b7a4872db46e69235876df70a9231
Source dataset
uspto-grants-2008_09
Patent number
US07429607B2

Reaction notes

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