1-(Chloromethoxy)-2-methoxyethane → HCID 86628073, compound

HRID 1622104Notes

Reaction equation

HRID 1622104 reaction equation
[Br:1][C:2]1[C:3]([OH:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].C(N(C(C)C)CC)(C)C.[CH3:20][O:21][CH2:22][CH2:23][O:24][CH2:25]Cl>ClCCl>[Br:1][C:2]1[C:3]([O:10][CH2:20][O:21][CH2:22][CH2:23][O:24][CH3:25])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 81531DiisopropylethylamineHCID 109105553-Bromo-2-hydroxybenzaldehyde

Product 1

HCID 86628073HCID 86628073, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Bromo-2-hydroxybenzaldehyde (1.5 g, 7.5 mmol) was dissolved in dichloromethane (25 mL) and diisopropylethylamine (2 mL, 11.3 mmol) was added to the solution. The mixture was stirred while 2-methoxyethoxymethyl chloride (0.94 mL, 8.3 mmol) was added dropwise. The mixture was stirred for 1 hour and then washed with 5% citric acid solution (5 mL) until the washings were acidic, dried and concentrated by evaporation. Product was purified from the residue by chromatography (silica gel, 30% ethyl acetate/hexanes) to give 3-bromo-2-(2-methoxy-ethoxymethoxy)benzaldehyde (1.7 g).

Workup

  1. additionwas added dropwise
  2. washwashed with 5% citric acid solution (5 mL) until the washings
  3. customdried
  4. concentrationconcentrated by evaporation
  5. customProduct was purified from the residue by chromatography (silica gel, 30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-53c501e73ee64193aa31f2e096f93198
Source dataset
uspto-grants-2014_07
Patent number
US08778625B2

Reaction notes

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