Carbon tetrabromide → HCID 86681714, compound

HRID 571306Notes

Reaction equation

HRID 571306 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][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:12]2=[O:27])[S:5]([CH3:8])(=[O:7])=[O:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:48]>C(Cl)Cl>[Br:48][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][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:12]2=[O:27])[S:5]([CH3:8])(=[O:7])=[O:6]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 86681713HCID 86681713, compound

Product 1

HCID 86681714HCID 86681714, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 2-(5-(N-(2-hydroxyethyl)methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetate (as obtained from Example 38, step 1, 1.12 g, 2.81 mmol) in DCM (20 ml), triphenylphosphine (0.958 g, 3.65 mmol) was added. After 10 minutes at room temperature under stirring, CBr4 (1.212 g, 3.65 mmol) was added, and the mixture was stirred at the same temperature for additional 14 hours. The volatiles were removed under vacuum and the crude was purified by chromatography on silica gel column (petroleum ether:ethyl acetate=7:3) affording tert-butyl 2-(5-(N-(2-bromoethyl)methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetate that crystallized on standing (0.980 g, 2.124 mmol, 76% yield).

Workup

  1. stirringthe mixture was stirred at the same temperature for additional 14 hours
  2. customThe volatiles were removed under vacuum
  3. customthe crude was purified by chromatography on silica gel column (petroleum ether:ethyl acetate=7:3)

Sources & evidence

ORD record
ord-ddf84368554041eea265b3f94abd7e5b
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

Loading…