Benzaldehyde → HCID 86652349, compound

HRID 1259131Notes

Reaction equation

HRID 1259131 reaction equation
[Br:1][C:2]1[C:3]([C:10]#[N:11])=[N:4][C:5]([Cl:9])=[C:6]([CH3:8])[CH:7]=1.[Li+].CC([N-]C(C)C)C.[CH:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1>[Br:1][C:2]1[C:3]([C:10]#[N:11])=[N:4][C:5]([Cl:9])=[C:6]([CH2:8][CH:20]([OH:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 2724682Lithium diisopropylamideHCID 86652350HCID 86652350, compound

Product 1

HCID 86652349HCID 86652349, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 3-bromo-6-chloro-5-methylpicolinonitrile (from the previous step) in THF (0.2 M) was cooled to −78° C. LDA (2N solution, 2 eq) was added dropwise. The reaction was kept stirring at −78° C. for 1 hour, followed by addition of benzaldehyde (1 eq). The reaction was kept stirring at −78° C. for another 30 minutes before allowing it to slowly warm to room temperature. The reaction was quenched with sat. NH4Cl and extracted with EtOAc. Combined organic washes were concentrated. Flash chromatography (silica gel, 20-50% EtOAc in hexanes) afforded the product 3-bromo-6-chloro-5-(2-hydroxy-2-phenylethyl)picolinonitrile as a yellow solid.

Workup

  1. stirringThe reaction was kept stirring at −78° C. for another 30 minutes
  2. temperatureto slowly warm to room temperature
  3. customThe reaction was quenched with sat. NH4Cl
  4. extractionextracted with EtOAc
  5. concentrationCombined organic washes were concentrated

Sources & evidence

ORD record
ord-c9ba00acb50a419cb383a31a6eea2bcf
Source dataset
uspto-grants-2013_06
Patent number
US08466167B2

Reaction notes

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