4-Methyloxybenzyl chloride → HCID 86708669, compound

HRID 921778Notes

Reaction equation

HRID 921778 reaction equation
[Br:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[C:4]([Cl:18])[CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH3:29][O:30][C:31]1[CH:38]=[CH:37][C:34]([CH2:35]Cl)=[CH:33][CH:32]=1>CN(C=O)C>[Br:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([N:10]([CH2:35][C:34]2[CH:37]=[CH:38][C:31]([O:30][CH3:29])=[CH:32][CH:33]=2)[C:11](=[O:17])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[C:4]([Cl:18])[CH:3]=1

Participants

5

Reactant 3

HCID 699934-Methyloxybenzyl chlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 86708665HCID 86708665, compound

Product 1

HCID 86708669HCID 86708669, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of tert-butyl (4-bromo-2-chloro-5-cyanophenyl)carbamate (1.0 g, 3.02 mmol) in DMF (10 mL) was cooled in an ice bath and NaHMDS (1 M solution in THF, 4.52 ml, 4.52 mmol) was added. After 20 min, 4-methoxybenzyl chloride (0.616 ml, 4.52 mmol) was added and the reaction was removed from the bath and left stirring at room temperature overnight. The reaction was partitioned between EtOAc and sat. aq. NH4Cl solution. The aqueous phase was extracted with EtOAc and the combined organic extracts were washed with brine. After drying with sodium sulfate, the solvents were removed and silica gel chromatography with hexane containing 0 to 30% EtOAc afforded tert-butyl (4-bromo-2-chloro-5-cyanophenyl)(4-methoxybenzyl)carbamate (1.04 g) as a white solid.

Workup

  1. customthe reaction was removed from the bath
  2. waitleft
  3. customThe reaction was partitioned between EtOAc and sat. aq. NH4Cl solution
  4. extractionThe aqueous phase was extracted with EtOAc
  5. washthe combined organic extracts were washed with brine
  6. dry with materialAfter drying with sodium sulfate
  7. customthe solvents were removed

Sources & evidence

ORD record
ord-268bd57962b44edc88af216801709a73
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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