Epibromohydrin → 2-{2-[4-(2-Chlorophenyl)butyl]phenoxymethyl}oxirane

HRID 743219Notes

Reaction equation

HRID 743219 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[OH:18].[CH3:19][C:20](C)([O-:22])[CH3:21].[K+].C(C1OC1)Br>CC(N(C)C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH2:19][CH:20]1[CH2:21][O:22]1

Participants

5

Reactant 3

HCID 18430EpibromohydrinHCID 194239572-[4-(2-Chlorophenyl)butyl]phenolHCID 23665647Potassium tert-butoxide

Product 1

HCID 194239262-{2-[4-(2-Chlorophenyl)butyl]phenoxymethyl}oxiraneYield 88.5%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Following a procedure similar to that described in Example 1(a), 800 mg of 2-[4-(2-chlorophenyl)butyl]phenol (prepared as described in Preparation 18), 344 mg of potassium t-butoxide and 835 mg of epibromohydrin were reacted in 20 ml of dimethylacetamide. The crude product, extracted as described in Example 1(a), was purified as described in Example 1(a), to give 860 mg (yield 88%) of the title compound as a colorless oil.

Workup

  1. extractionThe crude product, extracted
  2. customwas purified

Sources & evidence

ORD record
ord-3fc4a683d5784079aacd923c9d62ffc6
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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