Benzyl Bromide → HCID 13772341, compound

HRID 1710112Notes

Reaction equation

HRID 1710112 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH3:18])[C:3]1=[O:19].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1>[CH2:20]([C:4]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH3:18])[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:2]([CH3:1])[C:3]1=[O:19])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 105150342H-Indol-2-one, 1,3-dihydro-3-(2-methoxyphenyl)-1-methyl-

Product 1

HCID 13772341HCID 13772341, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

20.24 g (0.08 mol) of 1-methyl-3-(2-methoxyphenyl)indolin-2-one are dissolved in 200 ml of dry THF. Then 9.2 g (0.08 mol) of potassium tertiary-butylate are added, and the mixture is stirred at room temperature for 15 minutes. At 10°, a solution of 12.1 ml of benzyl bromide in 20 ml of dry THF is added dropwise, and the mixture is then stirred at room temperature for 3 hours. It is then concentrated in vacuo, the residue is partitioned between water and ethyl acetate, and the organic phase is washed twice with water, dried and concentrated. 26.1 g of product of melting point 174°-176° C. are obtained.

Workup

  1. stirringthe mixture is then stirred at room temperature for 3 hours
  2. concentrationIt is then concentrated in vacuo
  3. customthe residue is partitioned between water and ethyl acetate
  4. washthe organic phase is washed twice with water
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-304225871bbb4513ba78562269f6dc28
Source dataset
uspto-grants-1990_08
Patent number
US04952598

Reaction notes

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