Bromotrimethylsilane → 2-(5-(Bromomethyl)thiophen-2-yl)-5-chlorothiophene

HRID 1432842Notes

Reaction equation

HRID 1432842 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[S:8][C:9]([CH2:12]O)=[CH:10][CH:11]=2)=[CH:4][CH:3]=1.[Br:14][Si](C)(C)C>C(Cl)Cl>[Br:14][CH2:12][C:9]1[S:8][C:7]([C:5]2[S:6][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 69027048(5'-Chloro-[2,2']bithiophenyl-5-yl)-methanol

Product 1

HCID 690271222-(5-(Bromomethyl)thiophen-2-yl)-5-chlorothiopheneYield 58.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (5′-chloro-[2,2′]bithiophenyl-5-yl)-methanol (2.23 g, 9.66 mmol) in 65 mL of CH2Cl2 is added bromotrimethylsilane (3.82 mL, 29.0 mmol). After 4 h, the solution is concentrated in vacuo. The crude product is stirred in hot hexanes and filtered. The filtrate is concentrated and the title compound (1.67 g, 5.69 mmol) is obtained as a green solid. 1H NMR (CDCl3, 300 MHz) δ7.00 (d, 1H), 6.94 (m, 2H), 6.85 (d, 2H), 4.71 (s, 2H).

Workup

  1. concentrationthe solution is concentrated in vacuo
  2. filtrationfiltered
  3. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-1a01e452dcf444e5a72a2245dde6f233
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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