Carbon tetrabromide → (3-Bromopropoxy)(tert-butyl)dimethylsilane

HRID 726091Notes

Reaction equation

HRID 726091 reaction equation
Br[C:2]([Br:5])(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:25][Si:26]([CH3:36])([C:32]([CH3:35])([CH3:34])[CH3:33])[O:27][CH2:28][CH2:29]CO>C(Cl)Cl>[Br:5][CH2:2][CH2:29][CH2:28][O:27][Si:26]([CH3:36])([CH3:25])[C:32]([CH3:35])([CH3:34])[CH3:33]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 40777913-[(Tert-butyldimethylsilyl)oxy]propan-1-ol

Product 1

HCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilaneYield 86.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-25 °C

Procedure

5.44 g of tetrabromomethane and 4.30 g of triphenyl-phosphine were added to a solution of 2.5 g of the product of Step A in 27 ml of methylene chloride cooled down to -25° C. The reaction solution was stirred for 90 minutes at 0° C. and then was chromatographed on silica (eluant: ethyl acetate-cyclohexane 1-9) to obtain 2.885 g of the expected product.

Workup

  1. customwas chromatographed on silica (eluant: ethyl acetate-cyclohexane 1-9)

Sources & evidence

ORD record
ord-11075d22ff614571915843f896476ddc
Source dataset
uspto-grants-1998_01
Patent number
US05707982

Reaction notes

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