Water → 3-Bromo-5-methoxymethoxy-benzaldehyde

HRID 457534Notes

Reaction equation

HRID 457534 reaction equation
[Li]CCCC.Br[C:7]1[CH:12]=[C:11]([O:13][CH2:14][O:15][CH3:16])[CH:10]=[C:9]([Br:17])[CH:8]=1.CN([CH:21]=[O:22])C.O>CCOCC>[Br:17][C:9]1[CH:8]=[C:7]([CH:12]=[C:11]([O:13][CH2:14][O:15][CH3:16])[CH:10]=1)[CH:21]=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 192615801,3-Dibromo-5-(methoxymethoxy)benzeneHCID 178418339Butyllithium

Product 1

HCID 192615953-Bromo-5-methoxymethoxy-benzaldehydeYield 74%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

n-BuLi (8.34 mL of a 1.6 M solution in Et2O, 13.34 mmol) was added dropwise to a solution cooled to −78° C. of 1,3-dibromo-5-methoxymethoxy-benzene (3.59 g, 12.13 mmol) in anhydrous Et2O (40 mL) under a nitrogen atmosphere. The solution was aged at −78° C. for 45 m, anhydrous DMF (1.03 mL, 13.34 mmol) was added, and the reaction mixture was slowly warmed to RT. The mixture was poured into H2O (50 mL), and the aqueous phase was extracted with Et2O (2×75 mL). The combined organic fractions were washed with brine (50 mL) and dried over anhydrous MgSO4. The solvents were evaporated, and the remaining oil was purified by flash chromatography over silica gel (0% to 10% EtOAc/hexanes) to afford 2.18 g (74%) of 3-bromo-5-methoxymethoxy-benzaldehyde (113b).

Workup

  1. additionwas added
  2. extractionthe aqueous phase was extracted with Et2O (2×75 mL)
  3. washThe combined organic fractions were washed with brine (50 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. customThe solvents were evaporated
  6. customthe remaining oil was purified by flash chromatography over silica gel (0% to 10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-5d941e1dba994ae9b812599144400742
Source dataset
uspto-grants-2007_03
Patent number
US07189718B2

Reaction notes

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