تفاعل #1833289

معادلة التفاعل

sodium hydrogen carbonate

{4-chloro-2-[(phenylmethyl)oxy]phenyl}methanol

phosphorus tribromide

→

1-(bromomethyl)-4-chloro-2-[(phenylmethyl)oxy]benzene

المذيبات

DCM

DCM

water

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   أخرىat −10 to −15° C.
2. 2
   أخرىThe phases were separated
3. 3
   غسيلthe aqueous phase washed with DCM (30 ml)
4. 4
   غسيلThe combined organic extracts were washed with water (10 ml)
5. 5
   استخلاصThe organic extract
6. 6
   تجفيفwas dried (MgSO4)
7. 7
   ترشيحfiltered
8. 8
   أخرىthe solvent removed in vacuo

الإجراء التجريبي

To a solution of {4-chloro-2-[(phenylmethyl)oxy]phenyl}methanol (for a preparation see intermediate 6) (0.501 g, 2.02 mmol) in DCM (10 ml) at −10 to −15° C., under nitrogen, was added a solution of phosphorus tribromide (0.190 ml, 2.02 mmol, Aldrich) in DCM (5 ml) dropwise. The solution was allowed to warm to ambient temperature and stirred for 4.5 h. To the reaction mixture in an ice-water bath was added dropwise saturated aqueous sodium hydrogen carbonate (5 ml). The mixture was diluted with water (45 ml) and dichloromethane (55 ml). The phases were separated and the aqueous phase washed with DCM (30 ml). The combined organic extracts were washed with water (10 ml). The organic extract was dried (MgSO4), filtered and the solvent removed in vacuo to give 1-(bromomethyl)-4-chloro-2-[(phenylmethyl)oxy]benzene (0.505 g) as a colourless gum.

المصدر