Bromotrimethylsilane → HCID 17821887, compound

HRID 50050Notes

Reaction equation

HRID 50050 reaction equation
C[Si](Br)(C)C.[CH2:6]([N:8]([CH2:23][CH3:24])[C:9](=[O:22])[C:10]([CH2:12][O:13][CH2:14][CH2:15][P:16]([O:20]C)([O:18]C)=[O:17])=[CH2:11])[CH3:7]>>[CH2:23]([N:8]([CH2:6][CH3:7])[C:9](=[O:22])[C:10]([CH2:12][O:13][CH2:14][CH2:15][P:16]([OH:20])([OH:18])=[O:17])=[CH2:11])[CH3:24]

Participants

3

Reactant 2

HCID 76113BromotrimethylsilaneHCID 17821888HCID 17821888, compound

Product 1

HCID 17821887HCID 17821887, compoundYield 100%

Conditions

Temperature
40 °C

Procedure

17 g (111 mmol) trimethylsilyl bromide are slowly added dropwise to 13.5 g (51 mmol) of compound 2 and the mixture is subsequently stirred for 2 hours at 40° C. Afterwards, it is firstly concentrated in a water-jet vacuum and then in a fine vacuum (0.2 mbar), 70 ml of absolute methanol are added and the mixture is stirred overnight at room temperature. The slightly yellowish, clear solution is concentrated on the rotary evaporator and dried off in fine vacuum (0.2 mbar) at 40° C. until its weight is constant. 13.5 g (100% yield) of a bight yellow oil remain as product, which has a HPLC purity of 98.1%.

Workup

  1. concentrationAfterwards, it is firstly concentrated in a water-jet vacuum
  2. additionin a fine vacuum (0.2 mbar), 70 ml of absolute methanol are added
  3. stirringthe mixture is stirred overnight at room temperature
  4. concentrationThe slightly yellowish, clear solution is concentrated on the rotary evaporator
  5. customdried off in fine vacuum (0.2 mbar) at 40° C. until its weight

Sources & evidence

ORD record
ord-5307ba04924b43218eec07a74e212a4d
Source dataset
uspto-grants-2004_03
Patent number
US06710149B2

Reaction notes

Loading…