Chloromethyl Methyl Ether → 3-Bromo-2-(methoxymethoxy)benzaldehyde

HRID 84970Notes

Reaction equation

HRID 84970 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(CC)CC)C.[CH3:18][O:19][CH2:20]Cl>C(Cl)Cl>[Br:1][C:2]1[C:3]([O:10][CH2:18][O:19][CH3:20])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 8471TriethylamineHCID 109105553-Bromo-2-hydroxybenzaldehyde

Product 1

HCID 113685643-Bromo-2-(methoxymethoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3-bromo-2-hydroxybenzaldehyde (1.33 g, 6.6 mmol) in CH2Cl2 (10 mL) at 0° C. was added triethylamine (0.81 g, 8 mmol) then chloromethyl methyl ether (0.56 g, 7 mmol). The mixture was stirred for 45 minutes and partitioned between CH2Cl2 and saturated NaHCO3(aq). The crude material was purified by silica gel column chromatography eluting with hexanes and ethyl acetate (5:1) to afford the titled compound.

Workup

  1. custompartitioned between CH2Cl2 and saturated NaHCO3(aq)
  2. customThe crude material was purified by silica gel column chromatography
  3. washeluting with hexanes and ethyl acetate (5:1)

Sources & evidence

ORD record
ord-83066e9044f943cf9fd927ae5a28ed72
Source dataset
uspto-grants-2014_09
Patent number
US08846951B2

Reaction notes

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