Carbon tetrabromide → HCID 69385955, compound

HRID 916815Notes

Reaction equation

HRID 916815 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([S:9]([N:12]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1.C(Br)(Br)(Br)[Br:30].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:30][CH2:2][C:3]1[CH:4]=[C:5]([S:9]([N:12]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 468348293-(Hydroxymethyl)-N,N-bis{[2-(trimethylsilyl)ethoxy]methyl}benzenesulfonamide

Product 1

HCID 69385955HCID 69385955, compoundYield 25.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(Hydroxymethyl)-N,N-bis{[2-(trimethylsilyl)ethoxy]methyl}benzenesulfonamide (0.735 g) was stirred with ice-water cooling in dichloromethane (32 ml) under nitrogen and carbon tetrabromide (0.962 g) and triphenylphosphine (0.646 g) were added successively. After 5 min the cooling bath was removed and the mixture was stirred at 21° for 4 h. The mixture was poured onto an SPE silica cartridge (10 g). The cartridge was eluted with dichloromethane to give the title compound (0.21 g) LCMS RT=4.31 min.

Workup

  1. customAfter 5 min the cooling bath was removed
  2. additionThe mixture was poured onto an SPE silica cartridge (10 g)
  3. washThe cartridge was eluted with dichloromethane

Sources & evidence

ORD record
ord-ab09da478398422089cddb6b67194397
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

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