4-Methoxybenzyl bromide → HCID 86685930, compound

HRID 2277602Notes

Reaction equation

HRID 2277602 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[Cl:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[C:17](=[O:21])[NH:16][CH2:15]2.Br[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1>C1COCC1>[Cl:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[C:17](=[O:21])[N:16]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1)[CH2:15]2

Participants

5

Reactant 3

HCID 1650214-Methoxybenzyl bromideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 197881085-Chloro-2,3-dihydro-1H-isoindol-1-one

Product 1

HCID 86685930HCID 86685930, compoundYield 104.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium bis(trimethylsilyl) amide (2 mL, 2 M in THF, 2 mmol) was added dropwise at 0° C. to a solution of 5-chloro-2,3-dihydro-isoindol-1-one (0.34 g, 2 mmol) in THF (10 mL). After stirring for 10 min, 1-bromomethyl-4-methoxy-benzene (0.52 g, 2.6 mmol) was added dropwise. The resulting reaction mixture was allowed to stir at room temperature for 48 hours before quenching with saturated aqueous ammonium chloride solution. After extraction with EtOAc, the organic layer was washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give the crude product (0.6 g, 100%) as a yellow oil. MS: 288.0 (M+H+). It was used directly in the next step, without further purification.

Workup

  1. customThe resulting reaction mixture
  2. stirringto stir at room temperature for 48 hours
  3. custombefore quenching with saturated aqueous ammonium chloride solution
  4. extractionAfter extraction with EtOAc
  5. washthe organic layer was washed with brine
  6. customdried over anhy
  7. filtrationNa2SO4, filtered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e4c44a76365c4d8c842ecfd6ecd84be6
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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