Water → HCID 14557545, compound

HRID 2197473Notes

Reaction equation

HRID 2197473 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][Br:10])[CH:4]=1.[P:11]([O:18]CC)([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14].O>CN(C=O)C>[Br:10][CH2:9][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[CH2:2][P:11](=[O:18])([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 962WaterHCID 31215Triethyl phosphiteHCID 69373Benzene, 1,3-bis(bromomethyl)-

Product 1

HCID 14557545HCID 14557545, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of α,α′-Bisbromo-m-xylene (10.02 g, 37.95 mmol) in DMF (20 mL) was added triethyl phosphite (3.15 g, 3.3 mL, 19.98 mmol) via syringe. The mixture was heated to 150° C. for 2 minutes in a microwave. The reaction mixture was poured into water and product extracted with diethyl ether (3×25 mL). The combined organics were washed with water (2×50 mL) and brine (50 mL), and dried over Na2SO4. Reduced volume in vacuo and purified product by flash column eluting 30-100% ethyl acetate in hexanes to give 4.64 g (76%) 60 as a colorless oil. LCMS: m/z for C12H18BrO3P++H observed 321.0 and 323.0 at 2.29 minutes of a 3.5 minute run, gradient 5-95% CH3CN in H2O.

Workup

  1. extractionextracted with diethyl ether (3×25 mL)
  2. washThe combined organics were washed with water (2×50 mL) and brine (50 mL)
  3. dry with materialdried over Na2SO4
  4. custompurified product by flash column
  5. washeluting 30-100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-95335e65a34d4d88ad8d258673893239
Source dataset
uspto-grants-2012_12
Patent number
US08338593B2

Reaction notes

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