Iodoethane → 1-Bromo-2-chloro-4-ethoxybenzene

HRID 51021Notes

Reaction equation

HRID 51021 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[Cl:9].[H-].[Na+].I[CH2:13][CH3:14]>C1COCC1.CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:13][CH3:14])=[CH:4][C:3]=1[Cl:9]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 70181824-Bromo-3-chlorophenol

Product 1

HCID 227356231-Bromo-2-chloro-4-ethoxybenzeneYield 81.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

The 4-Bromo-3-chloro-phenol (24 mmol, 5 g) in anhydrous THF (50 mL) was added to a stirred solution of NaH (60% in mineral oil, 120 mmol, 4.8 g) in THF (100 mL) and DMF (42 mL) under N2 at room temperature. This solution stirred for 30 minutes. The iodoethane (240 mmol, 19.2 mL) was then added. The solution was stirred and was refluxed overnight. The reaction was cooled and quenched with 1 N HCl (150 mL), extracted into CH2Cl2 (2×150 mL), dried over MgSO4, concentrated in vacuo, and distilled under vacuum yielding 1-bromo-2-chloro-4-ethoxybenzene as a brown oil (4.59 g, 81%). 1H NMR (CDCl3, 300 MHz): δ7.42 (1H, d, J 8.7 Hz), 6.96 (1H, d, J 2.9 Hz), 6.64 (1H, dd, J 8.8 and 2.5 Hz), 3.95 (2H, q, J 7.0 Hz), 1.39 (3H, t, J 7.0 Hz.)

Workup

  1. stirringThe solution was stirred
  2. temperaturewas refluxed overnight
  3. temperatureThe reaction was cooled
  4. customquenched with 1 N HCl (150 mL)
  5. extractionextracted into CH2Cl2 (2×150 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. distillationdistilled under vacuum

Sources & evidence

ORD record
ord-2946c9d438cb4f04bb885094c294531a
Source dataset
uspto-grants-2004_03
Patent number
US06713471B1

Reaction notes

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