1,4-Dibromobenzene → Diethyl (4-bromophenyl)phosphonate

HRID 1181606Notes

Reaction equation

HRID 1181606 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][CH:3]=1.[P:9]([O-:16])([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12].C(N(CC)CC)C>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([P:9](=[O:16])([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12])=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 78041,4-DibromobenzeneHCID 8471TriethylamineHCID 3780918Diethylphosphite

Product 1

HCID 12625835Diethyl (4-bromophenyl)phosphonateYield 39.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

1,4-Dibromobenzene (2.36 g), diethyl phosphite (1.52 g) and triethylamine (1.53 ml) were dissolved in toluene, tetrakis(triphenylphosphine)palladium(0) (578 mg) was added, and the mixture was stirred at 80° C. for 2 hr. The reaction mixture was cooled to room temperature, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and brine, dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give the title compound (1.16 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed successively with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-fd8b6eb90cb649908d82560216722911
Source dataset
uspto-grants-2007_10
Patent number
US07285572B2

Reaction notes

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