3-Bromotoluene → Diethyl (3-methylphenyl)phosphonate

HRID 1531916Notes

Reaction equation

HRID 1531916 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=1.C([Li])(C)(C)C.[P:14](Cl)([O:19][CH2:20][CH3:21])([O:16][CH2:17][CH3:18])=[O:15]>O1CCCC1.CCCCC>[CH3:8][C:4]1[CH:3]=[C:2]([P:14]([O:19][CH2:20][CH3:21])(=[O:15])[O:16][CH2:17][CH3:18])[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 115603-BromotolueneHCID 13139Diethyl chlorophosphateHCID 178418306HCID 178418306, compound

Product 1

HCID 11020630Diethyl (3-methylphenyl)phosphonate

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 3-bromotoluene (5 g) in tetrahydrofuran at −78° C. was added tert-butyllithium (35 ml of a 1.7 M solution in pentane). The mixture was stirred at −78° C. for 1 hour and diethl chlorophosphate (5.1 ml) was added. After 2 hours the mixture was warmed to 0° C., quenched with aqueous ammonium chloride and partitioned between ethyl acetate and water. The organic phase was dried (MgSO4) and evaporated. Purified by chromatography eluting with 40% ethyl acetate in isohexane. Yield 2.7 g.

Workup

  1. temperatureAfter 2 hours the mixture was warmed to 0° C.
  2. customquenched with aqueous ammonium chloride
  3. custompartitioned between ethyl acetate and water
  4. dry with materialThe organic phase was dried (MgSO4)
  5. customevaporated
  6. customPurified by chromatography
  7. washeluting with 40% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-e144b492af0d46cebaa50b3277310e83
Source dataset
uspto-grants-2001_03
Patent number
US06200981B1

Reaction notes

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