Triethylamine → 2-(Trimethylsilyl)ethyl 3-bromo-2-thiophenecarboxylate

HRID 2222108Notes

Reaction equation

HRID 2222108 reaction equation
[Br:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([OH:9])=[O:8].O=S(Cl)Cl.C(N(CC)CC)C.[CH3:21][Si:22]([CH3:27])([CH3:26])[CH2:23][CH2:24]O>ClC(Cl)C>[Br:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([O:9][CH2:24][CH2:23][Si:22]([CH3:27])([CH3:26])[CH3:21])=[O:8]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 180132-(Trimethylsilyl)ethanolHCID 24386Thionyl ChlorideHCID 27396883-Bromothiophene-2-carboxylic acid

Product 1

HCID 223492282-(Trimethylsilyl)ethyl 3-bromo-2-thiophenecarboxylate

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A solution of 3-bromothiophene-2-carboxylic acid (1 mmol) and SOCl2 (3 mmol) in 1 mL of dichloroethane was heated at 80° C. for 20 h and then the solvents evaporated. The residue was dissolved in 2 mL CH2Cl2 and mixed with triethylamine (3 mmol) and 2-(trimethylsilyl)ethanol (1.3 mmol) at rt for 12 h. Extractive isolation provided 2-(trimethylsilyl)ethyl 3-bromo-2-thiophenecarboxylate as an oil.

Workup

  1. customthe solvents evaporated
  2. dissolutionThe residue was dissolved in 2 mL CH2Cl2

Sources & evidence

ORD record
ord-e9fb06033bae4d0a941edf989db7e02b
Source dataset
uspto-grants-2008_05
Patent number
US07371739B2

Reaction notes

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