Water → 5-(Bromomethyl)benzo[d]oxazole

HRID 1955167Notes

Reaction equation

HRID 1955167 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]=[N:7][C:6]=2[CH:10]=1.[Br:11]N1C(=O)CCC1=O.O>C(Cl)(Cl)Cl>[Br:11][CH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]=[N:7][C:6]=2[CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 27249705-Methylbenzoxazole

Product 1

HCID 219849815-(Bromomethyl)benzo[d]oxazole

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 5-methylbenzoxazole (0.5 g) in chloroform (20 ml) containing N-bromosuccinimide (0.18 g) and azoisobutyronitrile (0.05 g) was refluxed for 2 hours. After allowing to cool to room temperature the reaction mixture was treated with water (30 ml). The organic phase was separated and the aqueous phase extracted with dichloromethane (30 ml). The combined organic phases were washed with brine (30 ml), dried over magnesium sulphate and evaporated. The residue was triturated with pentane giving the title compound (0.36 g) as an off-white solid, m.p. 90-93° C.

Workup

  1. temperaturewas refluxed for 2 hours
  2. customThe organic phase was separated
  3. extractionthe aqueous phase extracted with dichloromethane (30 ml)
  4. washThe combined organic phases were washed with brine (30 ml)
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe residue was triturated with pentane giving the title compound (0.36 g) as an off-white solid, m.p. 90-93° C.

Sources & evidence

ORD record
ord-c67381d35b784eafaa91436b7cd95019
Source dataset
uspto-grants-2000_09
Patent number
US06124343

Reaction notes

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