Lithium Bromide → HCID 59343396, compound

HRID 2168169Notes

Reaction equation

HRID 2168169 reaction equation
[Br-:1].[Li+].[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([O:13][C@@H:14]2[CH2:18][O:17][C@@H:16]3[C@@H:19](OS(C4C=CC(C)=CC=4)(=O)=O)[CH2:20][O:21][C@H:15]23)(=[O:12])=[O:11])=[CH:6][CH:5]=1>CS(C)=O.O>[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([O:13][C@H:14]2[CH2:18][O:17][C@@H:16]3[C@@H:19]([Br:1])[CH2:20][O:21][C@H:15]23)(=[O:12])=[O:11])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 82050Lithium BromideHCID 11015881HCID 11015881, compound

Product 1

HCID 59343396HCID 59343396, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

Lithium bromide (19.2 g, 220.2 mmol) was added to a stirred solution of ditosylate (42) (40.0 g, 88.1 mmol) in dimethyl sulfoxide (200 mL) under an atmosphere of argon. The mixture was heated at 110° C. for 8 hours then at 120° C. for 1.75 hours. The mixture was diluted with water (500 mL) then extracted with tert-butyl methyl ether (4×250 mL). The organic phase was washed with water (3×250 mL) then brine (250 mL), dried (MgSO4), filtered and reduced in vacuo to leave an orange solid. Recrystallisation from methanol (100 mL) gave bromotosylate (47) (17.47 g, 55%) as a pale yellow solid. [α]D15+49.5° (c=11.7, CHCl3).

Workup

  1. extractionthen extracted with tert-butyl methyl ether (4×250 mL)
  2. washThe organic phase was washed with water (3×250 mL)
  3. dry with materialbrine (250 mL), dried (MgSO4)
  4. filtrationfiltered
  5. customto leave an orange solid
  6. customRecrystallisation from methanol (100 mL)

Sources & evidence

ORD record
ord-548ecb07976d491e9c2512f008a46fd8
Source dataset
uspto-grants-2015_06
Patent number
US09045492B2

Reaction notes

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