Water → 3-Bromo-5-methoxybenzaldehyde

HRID 457537Notes

Reaction equation

HRID 457537 reaction equation
Br[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([Br:10])[CH:3]=1.[Li]CCCC.CN([CH:19]=[O:20])C.O>CCOCC>[Br:10][C:4]1[CH:3]=[C:2]([CH:7]=[C:6]([O:8][CH3:9])[CH:5]=1)[CH:19]=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 110218123,5-DibromoanisoleHCID 178418339Butyllithium

Product 1

HCID 106086983-Bromo-5-methoxybenzaldehydeYield 96.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 1,3-dibromo-5-methoxybenzene (15 g, 56.40 mmol) in anhydrous Et2O (200 mL) under nitrogen was cooled to −78° C. n-BuLi (38.80 mL of a 1.6 M solution in Et2O, 62.00 mmol) was added dropwise, and the solution was aged at −78° C. for 45 m. To the resulting heterogeneous mixture was added anhydrous DMF (4.78 mL, 62.00 mmol), and the solution was slowly warmed to RT. The mixture was poured into H2O (200 mL), and the aqueous phase was extracted with Et2O (3×125 mL). The combined organic fractions were washed with brine (100 mL) and dried over anhydrous MgSO4. Evaporation of the solvent provided 11.70 g (96%) of 3-bromo-5-methoxybenzaldehyde (115).

Workup

  1. additionwas added dropwise
  2. customwas aged at −78° C. for 45 m
  3. extractionthe aqueous phase was extracted with Et2O (3×125 mL)
  4. washThe combined organic fractions were washed with brine (100 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-0777ce5184c4486e8b714d0b9d642a67
Source dataset
uspto-grants-2007_03
Patent number
US07189718B2

Reaction notes

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