Propargyl bromide → 1-(Prop-2-ynyloxy)-2-(trifluoromethoxy)benzene

HRID 1911281Notes

Reaction equation

HRID 1911281 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[C:20]#[CH:21]>C(#N)C.O>[CH2:21]([O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[O:3][C:2]([F:11])([F:12])[F:1])[C:20]#[CH:19]

Participants

6

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 27772992-(Trifluoromethoxy)phenol

Product 1

HCID 233934371-(Prop-2-ynyloxy)-2-(trifluoromethoxy)benzeneYield 107.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-trifluoromethoxyphenol (10.0 g, 56.1 mmol) in acetonitrile (120 mL) was added potassium carbonate (9.31 g, 67.4 mmol) and propargyl bromide (80% in toluene, 10.0 g, 7.70 mL, 67.4 mmol). The reaction was stirred at ambient temperature for seven days, then diluted with water (150 mL) and extracted with diethyl ether (300 mL). The organic layer was separated and concentrated to obtain the title compound (13.05 g) which was used without further purification in the next step. 1H NMR (300 MHz, CDCl3) δ 7.30-7.23 (m, 2H), 7.19-7.13 (m, 1H), 7.04-6.95 (m, 1H), 4.77 (d, J=2.4 Hz, 2H), 2.53 (t, J=2.4 Hz, 1H).

Workup

  1. extractionextracted with diethyl ether (300 mL)
  2. customThe organic layer was separated
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-154f029978d34d4c9893f1e9e39921c6
Source dataset
uspto-grants-2013_12
Patent number
US08604053B2

Reaction notes

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