Chloromethyl Methyl Ether → HCID 66666521, compound

HRID 1049668Notes

Reaction equation

HRID 1049668 reaction equation
[H-].[Na+].[NH2:3][C:4]1[C:5]([Br:11])=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1.[CH3:12][O:13][CH2:14]Cl>C1COCC1>[Br:11][C:5]1[C:6]([O:10][CH2:12][O:13][CH3:14])=[CH:7][CH:8]=[CH:9][C:4]=1[NH2:3]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 4592403-Amino-2-bromophenol

Product 1

HCID 66666521HCID 66666521, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

20.0 g (500 mmol) of sodium hydride (60% by weight in mineral oil) are added in portions to a solution of 94.0 g (500 mmol) of 3-amino-2-bromophenol [100367-36-0] in 1000 ml of THF, and the mixture is stirred until the evolution of gas is complete. 38.0 ml (500 mmol) of methoxymethyl chloride [107-30-2] are then added dropwise, and the mixture is stirred at 60° C. for a further 6 h. After cooling, the THF is removed in vacuo, the residue is taken up in 1000 ml of dichloromethane, the organic phase is washed twice with 300 ml of 0.1N NaOH each time, once with 300 ml of saturated sodium chloride solution, dried over potassium carbonate, and the solvent is removed in vacuo. Yield: 112.6 g (485 mmol), 97%. Purity: 99.0% (NMR).

Workup

  1. stirringthe mixture is stirred at 60° C. for a further 6 h
  2. temperatureAfter cooling
  3. customthe THF is removed in vacuo
  4. washthe organic phase is washed twice with 300 ml of 0.1N NaOH each time
  5. dry with materialonce with 300 ml of saturated sodium chloride solution, dried over potassium carbonate
  6. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-7f79ef70737d49738c1680b37a420599
Source dataset
uspto-grants-2016_07
Patent number
US09382253B2

Reaction notes

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