Phosphorus tribromide → Methyl 3-(1-bromoethyl)benzoate

HRID 714459Notes

Reaction equation

HRID 714459 reaction equation
O[CH:2]([C:4]1[CH:5]=[C:6]([C:10]([O:12][CH3:13])=[O:11])[CH:7]=[CH:8][CH:9]=1)[CH3:3].P(Br)(Br)[Br:15]>C1(C)C=CC=CC=1>[Br:15][CH:2]([C:4]1[CH:5]=[C:6]([C:10]([O:12][CH3:13])=[O:11])[CH:7]=[CH:8][CH:9]=1)[CH3:3]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 20428670Methyl 3-(1-Hydroxyethyl)benzoate

Product 1

HCID 20428675Methyl 3-(1-bromoethyl)benzoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5 g (27.75 mmol) of methyl 3-(1-hydroxyethyl)benzenecarboxylate (Example 60A) were initially charged in 100 ml of toluene. At 0° C., 0.98 g (36.07 mmol) of phosphorus tribromide were added dropwise, and the mixture was stirred at RT for 45 min. The reaction solution was poured onto ice-water and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and evaporated. The residue was purified by column chromatography on silica gel 60 (mobile phase:cyclohexane:ethyl acetate 50:1→40:1).

Workup

  1. additionThe reaction solution was poured onto ice-water
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel 60 (mobile phase:cyclohexane:ethyl acetate 50:1→40:1)

Sources & evidence

ORD record
ord-f7bd79ba38e24e25b062f14826c49efd
Source dataset
uspto-grants-2015_11
Patent number
US09187428B2

Reaction notes

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