1-(9,10-Dihydrophenanthren-2-yl)ethanone → 2-Bromoethyl-9,10-dihydrophenanthrene

HRID 374549Notes

Reaction equation

HRID 374549 reaction equation
C([C:4]1[CH:17]=[CH:16][C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:8][CH2:7][C:6]=2[CH:5]=1)(=O)C.[Br-:18].[Br-].[Br-].[C:21]1([N+](C)(C)C)[CH:26]=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1>C1COCC1>[Br:18][CH2:26][CH2:21][C:11]1[C:12]2[CH2:13][CH2:14][C:15]3[C:6](=[CH:5][CH:4]=[CH:17][CH:16]=3)[C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 2202091-(9,10-Dihydrophenanthren-2-yl)ethanoneHCID 17977687Phenyltrimethylammonium bromide dibromide

Product 1

HCID 189972702-Bromoethyl-9,10-dihydrophenanthrene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5.56 (25 mmol) of (8) in 100 mL of THF, 9.78 g (26 mmol) of phenyltrimethylammonium tribromide was added. After stirring for 20 min, the solution became pale yellow and a precipitate of phenyltrimethylammonium bromide separated. Water (300 mL) was added and the mixture was extracted with ethyl acetate. The extract was washed with water and evaporated to dryness to yield (28) which was further purified by trituration with ether and recrystallized from methanol to furnish pure (28), 5.66 g; m.p. 82°-83° C.

Workup

  1. customa precipitate of phenyltrimethylammonium bromide separated
  2. additionWater (300 mL) was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-75bc6883bf3a4ecf818b29e1f9b9d326
Source dataset
uspto-grants-1996_01
Patent number
US05480913

Reaction notes

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