Water → 2-Bromo-4-(tert-butyl)-1-((2-methoxyethoxy)methoxy)benzene

HRID 929553Notes

Reaction equation

HRID 929553 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[OH:12].C(N(CC)CC)C.[CH3:20][O:21][CH2:22][CH2:23][O:24][CH2:25]Cl.O>ClCCl>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:9])([CH3:11])[CH3:10])[CH:5]=[CH:4][C:3]=1[O:12][CH2:20][O:21][CH2:22][CH2:23][O:24][CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 751472-Bromo-4-tert-butylphenol2×HCID 775901-(Chloromethoxy)-2-methoxyethane

Product 1

HCID 867185612-Bromo-4-(tert-butyl)-1-((2-methoxyethoxy)methoxy)benzeneYield 72.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-bromo-4-(tert-butyl)phenol [Intermediate 1, Step 1] (5.0 g, 21.8 mmol) and triethylamine (4.4 g, 43.5 mmol) in anhydrous dichloromethane (20 mL) at room temperature under nitrogen was added dropwise 2-methoxyethoxymethyl chloride (2.5 mL, 21.9 mmol) and the reaction mixture stirred overnight. The reaction mixture was poured into water (100 mL), the organic phase separated, dried (MgSO4), filtered and concentrated under reduced pressure to give 2-bromo-4-(tert-butyl)-1-((2-methoxyethoxy)methoxy)benzene (5.0 g, 72% yield).

Workup

  1. customthe organic phase separated
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-db6d0b3bb13141bfb824d99a6b3398f6
Source dataset
uspto-grants-2016_03
Patent number
US09296696B2

Reaction notes

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