Water → HCID 66642878, compound

HRID 1171003Notes

Reaction equation

HRID 1171003 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([N:9]([CH3:11])[CH3:10])[CH:3]=1.C(N(C(C)C)C(C)C)C.Cl[CH2:22][O:23][CH3:24].O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:22][O:23][CH3:24])=[C:4]([N:9]([CH3:11])[CH3:10])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 23090743HCID 23090743, compound

Product 1

HCID 66642878HCID 66642878, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 4-bromo-2-dimethylamino-phenol (3.7 g, 17.13 mmol) in CH2Cl2 (100 mL) at room temperature was added ethyl-diisopropyl-amine (4.47 mL, 25.7 mmol) and chloro-methoxy-methane (1.69 mL, 22.27 mmol). The mixture was refluxed for 16 hrs, added water. The organic layer was collected and dried over Na2SO4, filtered and concentrated under reduced pressure to afford crude N-(5-bromo-2-methoxymethoxyphenyl)dimethylamine as a red oil (4.4 g, 99%): 1H NMR (200 MHz, DMSO-d6): 6.96 (m, 3 H), 5.17 (s, 2 H), 3.40 (s, 3 H), 2.72 (s, 6 H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=15% ethyl acetate in hexanes; Rf=0.59.

Workup

  1. temperatureThe mixture was refluxed for 16 hrs
  2. customThe organic layer was collected
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b0ad9313e8dc441587ed6497fc5529a5
Source dataset
uspto-grants-2010_11
Patent number
US07829552B2

Reaction notes

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