Methyl iodide → Methyl 2-(4-bromophenyl)acetate

HRID 2175383Notes

Reaction equation

HRID 2175383 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.N12CCCNC1CCCC=[CH:13]2.IC>C(#N)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:13])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 74654Benzeneacetic acid, 4-bromo-HCID 98128211,8-Diazabicyclo[5.4.0]undec-2-ene

Product 1

HCID 316783Methyl 2-(4-bromophenyl)acetateYield 79.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

20 ml acetonitrile was added to 4-bromophenylacetic acid (2 g, 9.3 mmol) and 1,8-diazabicyclo[5.4.0]undec-2-ene (1.7 g, 11.2 mmol) was added at 0° C. Iodomethane (1.98 g, 14.0 mmol) was slowly dropped to the mixture and stirred for 2 hours at room temperature. After the reaction is complete, the mixture was extracted using water (100 ml×2) and dichloromethane (100 ml). The title compound (1.7 g, 75%) was obtained by column chromatography (ethylacetate/n-hexane, 1/15).

Workup

  1. additionwas added at 0° C
  2. extractionthe mixture was extracted

Sources & evidence

ORD record
ord-8d1585e6987a4c46911c4318e2191c69
Source dataset
uspto-grants-2015_06
Patent number
US09062066B2

Reaction notes

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