Water → 4-Chloro-2-ethynyl-1-methoxybenzene

HRID 1776804Notes

Reaction equation

HRID 1776804 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:14][CH3:15])=[C:6]([C:8]#[C:9][Si](C)(C)C)[CH:7]=1.C([O-])([O-])=O.[K+].[K+].O>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:14][CH3:15])=[C:6]([C:8]#[CH:9])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 68489883[2-(5-Chloro-2-methoxyphenyl)ethynyl]trimethylsilane

Product 1

HCID 232607034-Chloro-2-ethynyl-1-methoxybenzeneYield 88.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

((5-chloro-2-methoxyphenyl)ethynyl)trimethylsilane (0.4 g, 1.7 mmol) was dissolved in MeOH (1 mL), K2CO3 (0.69 g, 5 mol) was added to it. Then the mixture was stirred at 25° C. for 1 hour, and added to H2O (50 mL). The mixture was extracted with ethyl acetate and washed with brine, dried over Na2SO4. After the combined organic layers were concentrated, the resulting residue was purified using prep-TLC (petroleum ether:EtOAc=10:1) to provide the product of 4-chloro-2-ethynyl-1-methoxybenzene (0.25 g, yield: 80%). 1H-NMR (CDCl3, 400 MHz) δ 7.43 (s, 1H), 7.28˜7.29 (m, 1H), 6.81˜6.85 (m, 1H), 3.89 (s, 3H), 3.34 (s, 1H). MS (M+H)+: 167/169.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationAfter the combined organic layers were concentrated
  5. customthe resulting residue was purified

Sources & evidence

ORD record
ord-98758af6437b43d28ede7e53ee858796
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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