Carbon tetrabromide → HCID 56975661, compound

HRID 1870250Notes

Reaction equation

HRID 1870250 reaction equation
O[CH2:2][C@@H:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:6][CH2:5][CH2:4]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:44].C(=O)([O-])O.[Na+]>ClCCl>[Br:44][CH2:2][C@@H:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:6][CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 11359478HCID 11359478, compound

Product 1

HCID 56975661HCID 56975661, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (5S)-5-hydroxymethyl-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-benzazepine (1.33 g), triphenylphosphine (2.10 g), carbon tetrabromide (2.65 g) and dichloromethane (50 ml) is stirred at room temperature for 30 minutes. The reaction solution is poured into a saturated aqueous sodium hydrogen carbonate solution, and the mixture is extracted with dichloromethane. The extract is dried over sodium sulfate, and concentrated under reduced pressure to remove the solvent, and the resulting residue is purified by silica gel column chromatography (solvent; dichloromethane:n-hexane=4:1), and recrystallized from diethyl ether--n-hexane to give (5S)-5-bromomethyl-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-benzazepine (1.26 g).

Workup

  1. extractionthe mixture is extracted with dichloromethane
  2. dry with materialThe extract is dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto remove the solvent
  5. customthe resulting residue is purified by silica gel column chromatography (solvent; dichloromethane:n-hexane=4:1)
  6. customrecrystallized from diethyl ether

Sources & evidence

ORD record
ord-f2f374fca1894057a3166e98e8010bb5
Source dataset
uspto-grants-2000_08
Patent number
US06096736

Reaction notes

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