1-Bromopropane → 1-Iodo-4-propoxybenzene

HRID 625889Notes

Reaction equation

HRID 625889 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Br[CH2:10][CH2:11][CH3:12].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.O>[I:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:10][CH2:11][CH3:12])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 78401-BromopropaneHCID 10340Sodium CarbonateHCID 108944-Iodophenol

Product 1

HCID 132969221-Iodo-4-propoxybenzeneYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 4-iodophenol (3 g, 13.64 mmol), 1-bromopropane (1.845 g, 15.00 mmol), and sodium carbonate (7.54 g, 54.5 mmol) in DMF (30 mL) was stirred at 80° C. for 4 hrs. The reaction mixture was diluted with water (250 mL) and extracted with EtOAc (3×75 mL). The combined organic extracts were washed with 0.5M NaOH (2×50 mL), and water (2×50 mL), and then dried over MgSO4. The solvent was removed. The crude product (3.11 g) was obtained, which was directly used for the next reaction without further purification. 1H NMR (400 MHz, chloroform-d) δ 7.61-7.53 (m, 2H), 6.74-6.67 (m, 2H), 3.90 (t, J=6.5 Hz, 2H), 1.88-1.76 (m, 2H), 1.05 (t, J=7.4 Hz, 3H).

Workup

  1. extractionextracted with EtOAc (3×75 mL)
  2. washThe combined organic extracts were washed with 0.5M NaOH (2×50 mL), and water (2×50 mL)
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed

Sources & evidence

ORD record
ord-366ce2d833d5422c8c97f48f5b992598
Source dataset
uspto-grants-2016_04
Patent number
US09308236B2

Reaction notes

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