Dimethyl Sulfide → 2-Benzyloxybenzylbromide

HRID 2268799Notes

Reaction equation

HRID 2268799 reaction equation
[Br:1]N1C(=O)CCC1=O.CSC.[CH2:12]([O:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22]O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(Cl)Cl>[CH2:12]([O:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22][Br:1])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 18811Benzenemethanol, 2-(phenylmethoxy)-HCID 67184N-bromobutanimide

Product 1

HCID 15142522-Benzyloxybenzylbromide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of N-Bromosuccinimide (1.84 g, 10.36 mmol) in 50 mL of CH2Cl2 was cooled in a wet ice/acetone bath. Dimethyl sulfide (0.91 mL, 12.44 mmol) was added and the reaction stirred for 10 minutes. The product from Step L (1.48 g, 6.91 mmol) in 25 mL of CH2Cl2 was added and the reaction was stirred at 0° C. for 4.5 hours. The reaction was poured into water/ice and separated layers. The organic portion was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo to provide the benzyl bromide.

Workup

  1. stirringthe reaction was stirred at 0° C. for 4.5 hours
  2. customseparated layers
  3. washThe organic portion was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9ce32517d2b84da78b5b2d8af1d3f602
Source dataset
uspto-grants-2001_12
Patent number
US06329376B1

Reaction notes

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