2-Bromophenol → 2-bromophenyl propargyl ether

HRID 1844699Notes

Reaction equation

HRID 1844699 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[CH:9]#[C:10][CH2:11]Br.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:11][C:10]#[CH:9]

Participants

5

Reactant 3

HCID 72442-BromophenolHCID 7842Propargyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 109875512-bromophenyl propargyl ether

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 2-bromophenol (50.0 g, 289 mmol) and progargyl bromide (41.3 g, 347 mmol) in dry ACN (500 mL) was added K2CO3 (47.9 g, 347 mmol) and the solution was stirred overnight at rt. The solvent was removed and the residue was poured into water and extracted with Et2O. The combined organic layers were dried over Na2SO4, filtered and concentrated to give compound P34a (60 g, 98%) as an oil.

Workup

  1. customThe solvent was removed
  2. additionthe residue was poured into water
  3. extractionextracted with Et2O
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give compound P34a (60 g, 98%) as an oil

Sources & evidence

ORD record
ord-d32775b0538a40a0a084c249fe57cea2
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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