Triethylamine → (2-Bromoethoxy)-tert-butyldimethylsilane

HRID 1108027Notes

Reaction equation

HRID 1108027 reaction equation
[Br:1][CH2:2][CH2:3][OH:4].[Si:5](Cl)([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:7])[CH3:6].CCN(CC)CC>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Si:5]([O:4][CH2:3][CH2:2][Br:1])([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:7])[CH3:6]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 108982-BromoethanolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneYield 96.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

Treat 2-bromoethanol (107 g) in CH2Cl2 (2 L) at 0° C. with t-butyidimethylsilylchloride (143 g), NEt3 (130 g) and DMAP (11 g), allow the reaction mixture to warm to 23° C. and stir for 18 h. Wash the mixture with H2O (250 mL), 20% HCl (250 mL), 20% NH4OH (250 mL), dry (MgSO4) and concentrate to give 2-(t-butyidimethylsilyloxy)-ethylbromide (197 g).

Workup

  1. washWash the mixture with H2O (250 mL), 20% HCl (250 mL), 20% NH4OH (250 mL)
  2. dry with materialdry (MgSO4)
  3. concentrationconcentrate

Sources & evidence

ORD record
ord-d83e2ea586bf4a96a9d8aeb6acb4e21a
Source dataset
uspto-grants-2000_05
Patent number
US06063926

Reaction notes

Loading…