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

HRID 1764897Notes

Reaction equation

HRID 1764897 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[Cl:9].[H-].[Na+].CN(C=O)C.I[CH2:18][CH3:19]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:18][CH3:19])=[CH:4][C:3]=1[Cl:9]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 70181824-Bromo-3-chlorophenol

Product 1

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

Reagents, catalysts & solvents 1

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

Sources & evidence

ORD record
ord-1dcc9bad6cd64b4b8ca18fa0e55013fd
Source dataset
uspto-grants-2007_06
Patent number
USRE039679E1

Reaction notes

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