Epibromohydrin → 2-{2-[4-(3-Chlorophenyl)butyl]phenoxymethyl}-oxirane

HRID 743222Notes

Reaction equation

HRID 743222 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[OH:18])[CH:5]=[CH:6][CH:7]=1.[CH3:19][C:20](C)([O-:22])[CH3:21].[K+].C(C1OC1)Br>CC(N(C)C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH2:19][CH:20]2[CH2:21][O:22]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 18430EpibromohydrinHCID 194238562-[4-(3-Chlorophenyl)butyl]phenolHCID 23665647Potassium tert-butoxide

Product 1

HCID 105434832-{2-[4-(3-Chlorophenyl)butyl]phenoxymethyl}-oxiraneYield 86.5%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Following a procedure similar to that described in Example 1(a), 800 mg of 2-[4-(3-chlorophenyl)butyl]phenol (prepared as described in Preparation 17), 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 840 mg (yield 86%) of the title compound as a colorless oil.

Workup

  1. extractionThe crude product, extracted
  2. customwas purified

Sources & evidence

ORD record
ord-b80746e923ef40a5bfcd12964727d92a
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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