Phosphorus tribromide → 1-(Bromomethyl)-4-ethynylbenzene

HRID 1401123Notes

Reaction equation

HRID 1401123 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7]O)=[CH:5][CH:4]=1)#[CH:2].P(Br)(Br)[Br:12]>C(Cl)Cl>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7][Br:12])=[CH:5][CH:4]=1)#[CH:2]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 11170993(4-Ethynylphenyl)methanol

Product 1

HCID 534266101-(Bromomethyl)-4-ethynylbenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Ethynylbenzyl alcohol a (1 g, 7.57 mmol) was diluted in 20 ml DCM, and cooled to 0° in ice bath. Phosphorus tribromide (4.1 g, 15 mmol) was added dropwise. The reaction was allowed to warm to room temperature gradually, and stirred under nitrogen overnight. The reaction was quenched by addition of H2O in ice bath, extracted by DCM. Combined organic layers were washed with brine, dried over Na2SO4 and concentrated to dryness. The crude material was purified by chromatography (ISCO) using 100% hexane to give pure 4-ethynylbenzyl bromide b (220 mg). M+H+ 195.1

Workup

  1. temperaturecooled to 0° in ice bath
  2. customThe reaction was quenched by addition of H2O in ice bath
  3. extractionextracted by DCM
  4. washCombined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness
  7. customThe crude material was purified by chromatography (ISCO)

Sources & evidence

ORD record
ord-ff95e10914264fe285f7be72a60264fe
Source dataset
uspto-grants-2014_12
Patent number
US08907092B2

Reaction notes

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