Imidazole → [(4-Bromo-2-thienyl)methoxy]t-butyldimethylsilane

HRID 2078732Notes

Reaction equation

HRID 2078732 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:7][OH:8])[S:5][CH:6]=1.N1C=CN=C1.[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH2:7][O:8][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[S:5][CH:6]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 2795484(4-Bromo-2-thienyl)methanol

Product 1

HCID 10614666[(4-Bromo-2-thienyl)methoxy]t-butyldimethylsilaneYield 86.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-bromo-thiophen-2-yl)-methanol (25 g, 130 mmol) in dichloromethane was added imidazole (9.7 g, 142 mmol) followed by tert-butyldimethylsilyl chloride (23.4 g, 156 mmol). The white suspension was stirred at room temperature for 30 minutes. The insoluble was filtered off. The filtrate was concentrated. The residual oil was chromatographed through silica gel (n-heptane/dichloromethane, 90/10 as eluant) to produce (4-bromo-thiophen-2-ylmethoxy)-tert-butyl-dimethyl-silane [34.6 g, Intermediate (67)] as a yellowish oil. LC/MS: 307.0 (M+H), RT=4.38 minutes.

Workup

  1. filtrationThe insoluble was filtered off
  2. concentrationThe filtrate was concentrated
  3. customThe residual oil was chromatographed through silica gel (n-heptane/dichloromethane, 90/10 as eluant)

Sources & evidence

ORD record
ord-927e67863fad462e88fd38dcd98f4294
Source dataset
uspto-grants-2011_04
Patent number
US07928231B2

Reaction notes

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