Methyl iodide → HCID 23212442, compound

HRID 744121Notes

Reaction equation

HRID 744121 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]O)=[CH:4][CH:3]=1.CI.[H-].[Na+].[CH2:14]1[CH2:18][O:17][CH2:16][CH2:15]1>>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][CH2:16][O:17][CH2:18][CH2:14][C:15]2[CH:8]=[CH:9][C:2]([Br:1])=[CH:3][CH:4]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 701194-Bromobenzyl alcohol

Product 1

HCID 23212442HCID 23212442, compound

Procedure

4-Bromobenzylalcohol(5.0 g, 26.7 mmol) was dissolved in THF (130 ml) and methyl iodide added (6.7 ml, 107.0 mmol). Sodium hydride (1.20 g of 80% dispersion in oil, 40.1 mmol) was added in two portions while stirring at room temperature under nitrogen. After stirring for 2 hours, the solvents were removed in vacuo and the residue partitioned between water and ether. The water was reextracted with ether and the combined organic fractions were then washed with water and brine before drying (Na2SO4) and evaporating in vacuo to give 4-bromobenzylmethyl ether as an orange liquid (5.3 g, 26.4 mmol). δH (250 MHz, CDCl3) 3.39 (3H, s, CH3), 4.40 (2H, s, CH2), 7.21 (2H, d, J 7.5 Hz, Ar--H), 7.48 (2H, d, J 7.5 Hz, Ar--H).

Workup

  1. stirringAfter stirring for 2 hours
  2. customthe solvents were removed in vacuo
  3. customthe residue partitioned between water and ether
  4. washthe combined organic fractions were then washed with water and brine
  5. dry with materialbefore drying (Na2SO4)
  6. customevaporating in vacuo

Sources & evidence

ORD record
ord-8f76bb48152a4900a121ee30cbfc5e0a
Source dataset
uspto-grants-1996_09
Patent number
US05559125

Reaction notes

Loading…