Water → HCID 58911255, compound

HRID 1295800Notes

Reaction equation

HRID 1295800 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9]=[N:10][N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:4]([F:16])[CH:3]=1.C([N-]C(C)C)(C)C.CN([CH:27]=[O:28])C.O>C1COCC1>[Br:1][C:2]1[C:3]([CH:27]=[O:28])=[C:4]([F:16])[C:5]([N:9]=[N:10][N:11]2[CH2:12][CH2:13][CH2:14][CH2:15]2)=[C:6]([F:8])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 5062348DiisopropylamideHCID 58911280HCID 58911280, compound

Product 1

HCID 58911255HCID 58911255, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

In a 200 ml three necked flask fitted with a magnetic stirrer, under inert atmosphere, (4-bromo-2,6-difluoro-phenyl)-pyrrolidin-1-yl-diazene a8 (6.06 g, 0.021 mol.) in THF (50 ml) is added to a solution of diisopropylamide (2 M in THF, 12.5 ml) cooled at −78° C. After 2 h at this temperature, dry DMF (3.2 ml) is added to the green solution. After 1 h, it is poured into water (200 ml), extracted with ether (3×200 ml) and the organic phase is dried over MgSO4, filtered and concentrated in vacuo to give the crude aldehyde a9 (6.62 g, 99%).

Workup

  1. extractionextracted with ether (3×200 ml)
  2. dry with materialthe organic phase is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-648ebc66438346ab94ca57c206f1958b
Source dataset
uspto-grants-2007_07
Patent number
US07244747B2

Reaction notes

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