Sodium hydride → 5-Bromo-1-chloro-3-ethyl-2-(2-methoxy-ethoxymethoxy)-benzene

HRID 1453232Notes

Reaction equation

HRID 1453232 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[C:5]([OH:10])=[C:4]([Cl:11])[CH:3]=1.[H-].[Na+].[CH3:14][O:15][CH2:16][CH2:17][O:18][CH2:19]Cl>C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[C:5]([O:10][CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])=[C:4]([Cl:11])[CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 587626844-Bromo-2-chloro-6-ethylphenol

Product 1

HCID 587625135-Bromo-1-chloro-3-ethyl-2-(2-methoxy-ethoxymethoxy)-benzeneYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-Bromo-2-chloro-6-ethyl-phenol dissolved in THF (10 mL) was added to a cooled 0° C. suspension of NaH (0.43 g, 10.8 mmol, 60% dispersion in mineral oil) in THF (20 ml). After the addition was complete the reaction mixture was warmed up to room temperature and stirred for 30 mins. 2-Methoxyethoxymethyl chloride (1.34 mL, 11.7 mmol) was added and the reaction was stirred for 15 hours. The reaction mixture was quenched with 1N HCl and extracted with EtOAc. The organic layers were washed with brine, dried over Na2SO4 and concentrated to a yellow oil. Purification by flash column chromatography (0% to 10% EtOAc in hexanes) gave the title compound as a clear oil (2.4 g, 76%). 1H NMR (400 MHz, CDCl3): δ 1.21 (t, J=7.3 Hz, 3H), 2.70 (q, J=7.6 Hz, 2H), 3.40 (s, 3H), 3.61 (m, 2H), 3.98 (m, 2H), 5.15 (s, 2H), 7.24 (s, 1H), 7.37 (s, 1H).

Workup

  1. additionwas added to a cooled 0° C.
  2. additionAfter the addition
  3. stirringthe reaction was stirred for 15 hours
  4. customThe reaction mixture was quenched with 1N HCl
  5. extractionextracted with EtOAc
  6. washThe organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated to a yellow oil
  9. customPurification by flash column chromatography (0% to 10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-6db6789f1da94793874e6b93fbaa151b
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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