3-Bromo-4-hydroxybenzonitrile → 3-Bromo-4-[(2-methoxyethoxy)methoxy]benzonitrile

HRID 1752861Notes

Reaction equation

HRID 1752861 reaction equation
C(N(C(C)C)CC)(C)C.[Br:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[OH:19])[C:14]#[N:15].[CH3:20][O:21][CH2:22][CH2:23][O:24][CH2:25]Cl>ClCCl>[Br:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[O:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH3:25])[C:14]#[N:15]

Participants

5

Reactant 3

HCID 753413-Bromo-4-hydroxybenzonitrileHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 81531Diisopropylethylamine

Product 1

HCID 114034163-Bromo-4-[(2-methoxyethoxy)methoxy]benzonitrileYield 79.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diisopropylethylamine (21.8 mL, 151.5 mmol) was added slowly to a magnetically stirred solution of 3-bromo-4-hydroxybenzonitrile (10 g, 50.5 mmol) and 2-methoxyethoxymethyl chloride (6.9 mL, 60.6 mmol) in dichloromethane (100 mL) and the mixture was stirred at room temperature for 30 minutes. The mixture was washed with 5% citric acid solution until the washings were acidic, dried and concentrated. Product was purified from the residue by chromatography (silica gel, 30% ethyl acetate/hexanes) gave 3-bromo-4-(2-methoxyethoxymethoxy)-benzonitrile (11.5 g).

Workup

  1. washThe mixture was washed with 5% citric acid solution until the washings
  2. customdried
  3. concentrationconcentrated
  4. customProduct was purified from the residue by chromatography (silica gel, 30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-2ea78a09870444d887205e02dad15217
Source dataset
uspto-grants-2015_10
Patent number
US09162986B2

Reaction notes

Loading…