N-bromobutanimide → Ethyl 2-(3-(bromomethyl)phenyl)acetate

HRID 2112997Notes

Reaction equation

HRID 2112997 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH2:9]([O:11][C:12](=[O:21])[CH2:13][C:14]1[CH:15]=[C:16]([CH3:20])[CH:17]=[CH:18][CH:19]=1)[CH3:10]>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[CH2:9]([O:11][C:12](=[O:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][Br:1])[CH:15]=1)[CH3:10]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 96574Ethyl m-tolylacetate

Product 1

HCID 10563066Ethyl 2-(3-(bromomethyl)phenyl)acetateYield 33.2%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of N-bromo-succinimide (10.68 g, 60.0 mmol), m-tolyl-acetic acid ethyl ester (10.0 g, 56.1 mmol; available from Aldrich Chemical Company, Inc., Milwaukee, Wis.) and benzoyl peroxide (40 mg, 0.17 mmol) in carbon tetrachloride (250 mL) was heated at reflux under nitrogen for 36 h. The reaction mixture was filtered, evaporated, and purified by chromatography on silica gel, eluting with 0-100% dichloromethane in hexane to give (3-bromomethyl-phenyl)-acetic acid ethyl ester (4.79 g, 33%). MS m/z 257. 1HNMR (DMSO-d6): δ 7.2-7.35 (m, 4H), 4.50 (s, 2H), 4.18 (q, 2H), 3.62 (s, 2H), 1.28 (t, 3H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 36 h
  3. filtrationThe reaction mixture was filtered
  4. customevaporated
  5. custompurified by chromatography on silica gel
  6. washeluting with 0-100% dichloromethane in hexane

Sources & evidence

ORD record
ord-1767806421f64ea391086c3478312341
Source dataset
uspto-grants-2009_04
Patent number
US07524870B2

Reaction notes

Loading…