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

HRID 1854168Notes

Reaction equation

HRID 1854168 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].BrC1C2OCN(C(C)(C)C)CC=2C=C(C(C)(C)C)C=1.C(N(CC)CC)C.[CH3:39][O:40][CH2:41][CH2:42][O:43][CH2:44]Cl>ClCCl.O>[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][CH2:39][O:40][CH2:41][CH2:42][O:43][CH3:44]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 751472-Bromo-4-tert-butylphenolHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 867185598-bromo-3,6-di-tert-butyl-3,4-dihydro-2H-benzo[e][1,3]oxazine

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 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-2105ec3caf6b4c2d840749d53e4e87fc
Source dataset
uspto-grants-2015_02
Patent number
US08962657B2

Reaction notes

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