N-bromobutanimide → 2-Bromo-5-methoxybenzyl bromide

HRID 2416679Notes

Reaction equation

HRID 2416679 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH3:10].[Br:11]N1C(=O)CCC1=O>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH2:10][Br:11]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 1179151-Bromo-4-methoxy-2-methylbenzene

Product 1

HCID 35259512-Bromo-5-methoxybenzyl bromideYield 70.4%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

A mixture of 2-bromo-5-methoxytoluene (20 g, 0.10 mol), N-bromosuccinimide (19.6 g, 0.11 mol), benzoyl peroxide (1 g, 4 mmol), and methylene chloride (200 mL) was irradiated for 18 hr with a flood lamp to effect gentle reflux. The mixture was then cooled to −10° C. for several hours and the solution was decanted away from the precipitated succinimide. The solution was concentrated and the residue was crystallized from chloroform/hexane to give the title compound (19.7 g, 70%) as pale yellow prisms: 1H NMR (CDCl3) δ 7.45 (d, J=8.9 Hz, 1 H, 6.99 (d, J=3 Hz, 1 H, 6.74 (dd, J=8.9, 3 Hz, 1 H), 4.55 (s, 2 H) 3.80 (s, 3 H).

Workup

  1. customwas irradiated for 18 hr with a flood lamp
  2. customthe solution was decanted away from the precipitated succinimide
  3. concentrationThe solution was concentrated
  4. customthe residue was crystallized from chloroform/hexane

Sources & evidence

ORD record
ord-d9c00a857c7d496ca16eb27c03dd2580
Source dataset
uspto-grants-2004_11
Patent number
US06825188B2

Reaction notes

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