Carbon tetrabromide → HCID 86681722, compound

HRID 571314Notes

Reaction equation

HRID 571314 reaction equation
O[CH2:2][CH2:3][N:4]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[C:14](=[O:18])[N:13]([CH2:19][C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])[C:12]2=[O:30])[S:5]([CH3:8])(=[O:7])=[O:6].C(Br)(Br)(Br)[Br:32].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:32][CH2:2][CH2:3][N:4]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[C:14](=[O:18])[N:13]([CH2:19][C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])[C:12]2=[O:30])[S:5]([CH3:8])(=[O:7])=[O:6]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 86681721HCID 86681721, compound

Product 1

HCID 86681722HCID 86681722, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of benzyl 2-(5-(N-(2-hydroxyethyl)methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetate (0.690 g, 1.595 mmol) in DCM (18 ml), CBr4 (0.688 g, 2.075 mmol) was added stirring at room temperature. After few minutes triphenylphosphine (0.544 g, 2.075 mmol) was added, and the mixture was stirred at room temperature for 2 hours. The solvent was evaporated under vacuum and the crude was purified by flash chromatography on silica gel column (petroleum ether:ethyl acetate=60:40) affording benzyl 2-(5-(N-(2-bromoethyl)methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetate (0.759 g, 1.532 mmol, 96% yield, MS/ESI+ 494.8-496.7 [MH]+).

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. customThe solvent was evaporated under vacuum
  3. customthe crude was purified by flash chromatography on silica gel column (petroleum ether:ethyl acetate=60:40)

Sources & evidence

ORD record
ord-6c9ca1877de84974938565727832afaa
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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