Chloromethyl Methyl Ether → HCID 86718609, compound

HRID 1480643Notes

Reaction equation

HRID 1480643 reaction equation
[Br:1][C:2]1[C:3]([OH:14])=[C:4]([CH:7]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:9]=1)[CH:5]=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH3:21][O:22][CH2:23]Cl>CN(C)C=O>[Br:1][C:2]1[C:3]([O:14][CH2:21][O:22][CH3:23])=[C:4]([CH:7]=[C:8]([C:10]([CH3:11])([CH3:13])[CH3:12])[CH:9]=1)[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 71720963-Bromo-5-tert-butyl-2-hydroxybenzaldehyde2×

Product 1

HCID 86718609HCID 86718609, compoundYield 102.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3-bromo-5-(tert-butyl)-2-hydroxybenzaldehyde (5.80 g, 22.6 mmol) (Intermediate 8) and potassium carbonate (4.10 g, 29.4 mmol) in N,N-dimethylformamide (50 mL) at room temperature was added chloromethyl methyl ether (2.01 mL, 27.1 mmol) and the reaction mixture stirred for 3 days. The reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The organic phase was separated, dried (Na2SO4), filtered, and the solvent removed under reduced pressure to give 3-bromo-5-(tert-butyl)-2-(methoxymethoxy)benzaldehyde (7.00 g, 100%+DMF) as a yellow oil.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
  2. customThe organic phase was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-6571f83ca4c848e58de6197dcfb0df30
Source dataset
uspto-grants-2016_08
Patent number
US09409893B2

Reaction notes

Loading…