Ethanol → 1-(2-Bromoethoxy)-4-iodo-2-methylbenzene

HRID 1453622Notes

Reaction equation

HRID 1453622 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[OH:9].[Br:10][CH2:11][CH2:12]Br.[OH-].[Na+].C(O)C>ClCCl>[Br:10][CH2:11][CH2:12][O:9][C:3]1[CH:4]=[CH:5][C:6]([I:8])=[CH:7][C:2]=1[CH3:1]

Participants

6

Reactant 4

HCID 702EthanolHCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 1437134-Iodo-2-methylphenol

Product 1

HCID 222197891-(2-Bromoethoxy)-4-iodo-2-methylbenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-methyl-4-iodophenol (5.00 grams), 1,2-dibromoethane (2.76 mL), sodium hydroxide (1.3 grams) and ethanol (100 mL) was stirred at reflux for 5 hours before being poured into ice. The crude solid was dissolved in dichloromethane and washed with 1N NaOH. The organic layer was evaporated in vacuo to give 2-Bromo-1-(2-methyl-4-iodophenoxy)ethane Compound 21a as a tan solid. 1H NMR (CDCl3) δ 6.54 (d, 1H), 4.25 (t, 2H), 3.66 (t, 2H), 2.20 (s, 3H).

Workup

  1. temperatureat reflux for 5 hours
  2. additionbefore being poured into ice
  3. washwashed with 1N NaOH
  4. customThe organic layer was evaporated in vacuo

Sources & evidence

ORD record
ord-df018b2c6b2942d8b5ea001ac4347ba0
Source dataset
uspto-grants-2009_01
Patent number
US07476672B2

Reaction notes

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