Chloromethyl ethyl ether → HCID 11097178, compound

HRID 2253339Notes

Reaction equation

HRID 2253339 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[C:5]#[N:6].[H-].[Na+].[CH2:13]([O:15][CH2:16]Cl)[CH3:14]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:16][O:15][CH2:13][CH3:14])[C:5]#[N:6]

Participants

5

Reactant 3

HCID 18523Chloromethyl ethyl etherHCID 24758Sodium hydrideHCID 753413-Bromo-4-hydroxybenzonitrile

Product 1

HCID 11097178HCID 11097178, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 3-bromo-4-hydroxybenzonitrile (25 g, 125 mmol) in THF (375 mL) at room temperature was treated with 95% NaH (4.3 g, 170 mmol) in a few portions. The resulting slurry was heated to 60° C. for 30 minutes, treated with chloromethyl ethyl ether (25 g, 260 mmol), and the mixture was stirred at 60° C. for another 2 hours. The reaction was cooled to room temperature, concentrated to a slush, treated with water (200 mL), and filtered. The solid was dried for about 16 hours under vacuum in the presence of P2O5 to provide 30 g (95%) of the desired product. MS (DCI/NH3) m/z 273, 275 (M+H+NH3)+; 1H NMR (CDCl3) δ 7.84 (d, 1H), 7.56 (dd, 1H), 7.25 (d, 1H), 5.35 (s, 2H), 3.76 (q, 2H), 1.23 (t, 3H).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. concentrationconcentrated to a slush
  3. additiontreated with water (200 mL)
  4. filtrationfiltered
  5. dry with materialThe solid was dried for about 16 hours under vacuum in the presence of P2O5

Sources & evidence

ORD record
ord-6e4357cde00949ff8567d01a47863e43
Source dataset
uspto-grants-2008_01
Patent number
US07323570B2

Reaction notes

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