3-Methoxytoluene → 3-Methoxybenzyl bromide

HRID 716457Notes

Reaction equation

HRID 716457 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[CH:4]=1.C1C(=O)N([Br:17])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:17][CH2:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

4

Reactant 2

HCID 75303-MethoxytolueneHCID 67184N-bromobutanimide

Product 1

HCID 40672073-Methoxybenzyl bromideYield 75.8%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 122 g (1.0 mol) of 1-methoxy-3-methylbenzene in 900 ml of CCl4, 178 g (1.0 mol) of NBS and 1.0 g of (PhCO2)2 were added at room temperature. This mixture was refluxed for 3 h, cooled to room temperature, and the formed succinimide was filtered off. Succinimide was additionally washed by 2×150 ml of CCl4. The combined filtrate was evaporated to dryness, and the residue was distilled in vacuum, b.p. 112-125° C./8 mm Hg. This procedure gave 152.5 g of 1-(bromomethyl)-3-methoxybenzene contaminated with ca. 25% of the isomeric product, i.e. 1-bromo-4-methoxy-2-methylbenzene.

Workup

  1. temperatureThis mixture was refluxed for 3 h
  2. filtrationthe formed succinimide was filtered off
  3. washSuccinimide was additionally washed by 2×150 ml of CCl4
  4. customThe combined filtrate was evaporated to dryness
  5. distillationthe residue was distilled in vacuum, b.p. 112-125° C./8 mm Hg

Sources & evidence

ORD record
ord-2392db89c0b84a5b9daaf25a3bd5f05d
Source dataset
uspto-grants-2015_11
Patent number
US09187583B2

Reaction notes

Loading…