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

HRID 1480605Notes

Reaction equation

HRID 1480605 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-d931f571b3ab4be4acc2c30f498d3295
Source dataset
uspto-grants-2016_08
Patent number
US09409893B2

Reaction notes

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