Imidazole → 2-(2-Bromoethyl)naphthalene

HRID 1182512Notes

Reaction equation

HRID 1182512 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]N1C(=O)CCC1=O.[CH:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[CH:30][C:29]=1[CH2:38][CH2:39]O.N1C=CN=C1>ClCCl>[Br:20][CH2:39][CH2:38][C:29]1[CH:30]=[CH:31][C:32]2[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:28]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 738772-Naphthaleneethanol

Product 1

HCID 2282702-(2-Bromoethyl)naphthaleneYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of triphenylphosphine (0.57 g, 2.2 mmol) and N-bromosuccinimide (0.39 g, 2.2 mmol) in anhydrous dichloromethane (4 mL) was stirred for 10 minutes. 2-Naphthalenethanol (0.25 g, 1.45 mmol) was added, followed inmmediately by imidazole (0.25 g, 1.45 mmol) and the mixture was stirred at room temperature for 18 hours. The reaction mixture was partitioned between H2O and dichloromethane. The aqueous layer was extracted with diethyl ether (2×20 mL) and the combined organic extracts were dried over MgSO4 and evaporated to dryness. The crude residue was purified by column chromatography through a plug of silica gel eluting with 10% ethyl acetate in hexanes to afford a colorless solid 214 (0.29 g, 86%).

Workup

  1. customThe reaction mixture was partitioned between H2O and dichloromethane
  2. extractionThe aqueous layer was extracted with diethyl ether (2×20 mL)
  3. dry with materialthe combined organic extracts were dried over MgSO4
  4. customevaporated to dryness
  5. customThe crude residue was purified by column chromatography through a plug of silica gel eluting with 10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-6ec8bf7bad6b453bbb59e5e04af7f6cf
Source dataset
uspto-grants-2007_10
Patent number
US07288567B2

Reaction notes

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