Cesium carbonate → HCID 15380427, compound

HRID 1417243Notes

Reaction equation

HRID 1417243 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].Br[CH2:14][CH:15]([O:18][CH3:19])[O:16][CH3:17].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[C:5]([O:10][CH2:14][CH:15]([O:18][CH3:19])[O:16][CH3:17])=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 816722-Bromo-1,1-dimethoxyethaneHCID 2622385-Bromo-2-hydroxy-3-methoxybenzaldehyde

Product 1

HCID 15380427HCID 15380427, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A heterogeneous solution of 31 g (0.134 mol) of 5-bromo-2-hydroxy-3-methoxybenzaldehyde, 28 g (0.166 mol) of 2-bromo-1,1-dimethoxyethane and 49 g (0.150 mol) of caesium carbonate in 150 ml of dimethylformamide is heated at 160° C. for 3 hours. After returning to room temperature, the mixture is filtered. The filtrate is then evaporated under reduced pressure. The solid so obtained is taken up in 250 ml of dichloromethane and filtered again. The homogeneous solution is then washed twice with 200 ml of 0.1N hydrochloric acid each time and subsequently with 200 ml of a saturated sodium chloride solution. The organic phase is then dried over sodium sulphate and subsequently evaporated under reduced pressure, yielding the expected product.

Workup

  1. customAfter returning to room temperature
  2. filtrationthe mixture is filtered
  3. customThe filtrate is then evaporated under reduced pressure
  4. customThe solid so obtained
  5. filtrationfiltered again
  6. washThe homogeneous solution is then washed twice with 200 ml of 0.1N hydrochloric acid each time
  7. dry with materialThe organic phase is then dried over sodium sulphate
  8. customsubsequently evaporated under reduced pressure

Sources & evidence

ORD record
ord-70a8c6b09a2842749a61a781d16a7097
Source dataset
uspto-grants-1999_03
Patent number
US05877190

Reaction notes

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