Carbon tetrabromide → HCID 22247313, compound

HRID 1531969Notes

Reaction equation

HRID 1531969 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[C:8]([CH3:14])[CH:9]=[C:10]([CH3:13])[CH:11]=2)[CH:6]([CH2:15][CH2:16]O)[CH2:5]1)(=[O:3])[CH3:2].C(Br)(Br)(Br)[Br:19].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>CC#N>[C:1]([N:4]1[C:12]2[C:7](=[C:8]([CH3:14])[CH:9]=[C:10]([CH3:13])[CH:11]=2)[CH:6]([CH2:15][CH2:16][Br:19])[CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 222473161-Acetyl-3-(2-hydroxyethyl)-4,6-dimethylindoline

Product 1

HCID 22247313HCID 22247313, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Acetyl-3-(2-hydroxyethyl)-4,6-dimethylindoline (7.0 g) and CBr4 (9.9 g) were dissolved in CH3CN (70 ml), and Ph3P (9.4 g) was added, which was followed by stirring at room temperature for 30 min. CH3CN was evaporated under reduced pressure. AcOEt (100 ml) was added, and the mixture was washed with water and dried over anhydrous sodium sulfate. AcOEt was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: benzene/AcOEt=50/1-10/1) to give 5.4 g of 1-acetyl-3-(2-bromoethyl)-4,6-dimethyl-indoline.

Workup

  1. customCH3CN was evaporated under reduced pressure
  2. additionAcOEt (100 ml) was added
  3. washthe mixture was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAcOEt was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: benzene/AcOEt=50/1-10/1)

Sources & evidence

ORD record
ord-bb74fa7a031742c8abbfd0b352076fe0
Source dataset
uspto-grants-2001_03
Patent number
US06200988B1

Reaction notes

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