Water → 1,3-Dibromo-5-(methoxymethoxy)benzene

HRID 457533Notes

Reaction equation

HRID 457533 reaction equation
Cl[CH2:2][O:3][CH3:4].[Br:5][C:6]1[CH:7]=[C:8]([OH:13])[CH:9]=[C:10]([Br:12])[CH:11]=1.C(N(C(C)C)CC)(C)C.O>C(Cl)Cl>[Br:5][C:6]1[CH:7]=[C:8]([O:13][CH2:2][O:3][CH3:4])[CH:9]=[C:10]([Br:12])[CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 122803,5-DibromophenolHCID 81531Diisopropylethylamine

Product 1

HCID 192615801,3-Dibromo-5-(methoxymethoxy)benzeneYield 101%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Chloromethylmethyl ether (1.45 mL, 19.13 mmol) was added dropwise to a solution of 3,5-dibromophenol (4.38 g, 17.39 mmol) and diisopropylethylamine (3.63 mL, 20.90 mmol) in CH2Cl2 (40 mL) at 0° C. The mixture was warmed to RT, stirred for 16 h, and added to H2O (50 mL). The layers were separated, and the aqueous fraction was extracted with CH2Cl2 (2×50 mL). The combined organic fractions were washed with brine (25 mL), dried over anhydrous MgSO4, and the solvent was evaporated to provide 5.20 g (100%) of 1,3-dibromo-5-methoxymethoxy-benzene (113a).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous fraction was extracted with CH2Cl2 (2×50 mL)
  3. washThe combined organic fractions were washed with brine (25 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-e248151ad1eb4220b3c3e05021b5afac
Source dataset
uspto-grants-2007_03
Patent number
US07189718B2

Reaction notes

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