Sodium hydride → 4-Bromo-1-(2-methoxy-ethoxymethoxy)-2-trifluoromethyl-benzene

HRID 517943Notes

Reaction equation

HRID 517943 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]([F:14])([F:13])[F:12])[CH:5]=1.Cl[CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21]>C1COCC1.C(OCC)(=O)C>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21])=[C:6]([C:11]([F:12])([F:13])[F:14])[CH:5]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 142784o-Cresol, 4-bromo-alpha,alpha,alpha-trifluoro-

Product 1

HCID 576575554-Bromo-1-(2-methoxy-ethoxymethoxy)-2-trifluoromethyl-benzeneYield 78%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (6.55 g) was added in small portions to a solution of 4-bromo-2-(trifluoromethyl)phenol (32.9 g) in THF (150 ml). After stirring at room temperature for 10 minutes, 1-(chloromethoxy)-2-methoxyethane (17 g) was then added by syringe. The mixture was stirred at room temperature for 24 hours then diluted with ethyl acetate (300 mL) and washed with water. Organics were dried over sodium sulphate and solvent evaporated under reduced pressure. The resulting residue was columned on silica gel using heptane as eluant to afford 4-bromo-1-((2-methoxy-ethoxy)methoxy)-2-(trifluoromethyl)benzene (78% yield).

Workup

  1. stirringThe mixture was stirred at room temperature for 24 hours
  2. washwashed with water
  3. dry with materialOrganics were dried over sodium sulphate and solvent
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-02104602ddbe46f3accfd6231c900024
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

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