3,4-Dichlorobenzaldehyde → HCID 58046334, compound

HRID 2359329Notes

Reaction equation

HRID 2359329 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[O:10][CH3:11].C([Mg]Cl)(C)C.[Cl:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][C:25]=1[Cl:26])[CH:21]=[O:22].[NH4+].[Cl-]>C1COCC1>[Cl:17][C:18]1[CH:19]=[C:20]([CH:21]([OH:22])[C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=2[O:10][CH3:11])[CH:23]=[CH:24][C:25]=1[Cl:26]

Participants

6

Reactant 4

HCID 227103,4-DichlorobenzaldehydeHCID 25517Ammonium ChlorideHCID 225911814-Bromo-3-methoxybenzonitrileHCID 178418918HCID 178418918, compound

Product 1

HCID 58046334HCID 58046334, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-bromo-3-methoxybenzonitrile (606 mg, 2.86 mmol) in dry THF (10 mL) was added iso-propylmagnesium chloride (2 M in diethylether, 1.54 mL, 3.09 mmol) slowly via microsyringe. To the reaction mixture was added 3,4-dichlorobenzaldehyde (270 mg, 1.54 mmol) in dry THF (1 mL) via syringe. After 1 hour at room temperature saturated aqueous NH4Cl (20 mL) was added and the mixture extracted with EtOAc (3×20 mL). The combined organics were concentrated in vacuo and taken through to the next step as crude.

Workup

  1. extractionthe mixture extracted with EtOAc (3×20 mL)
  2. concentrationThe combined organics were concentrated in vacuo

Sources & evidence

ORD record
ord-3cfdf068e53d40da9d62ac3750d19fef
Source dataset
uspto-grants-2014_04
Patent number
US08685977B2

Reaction notes

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