1-(Bromomethyl)-3-chlorobenzene → HCID 23130459, compound

HRID 2080079Notes

Reaction equation

HRID 2080079 reaction equation
C([Li])CCC.Br[C:7]1[S:11][C:10]([CH:12]2[O:16][CH2:15][CH2:14][O:13]2)=[CH:9][CH:8]=1.[Cl:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH2:21]Br>O1CCCC1>[Cl:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH2:21][C:7]1[S:11][C:10]([CH:12]2[O:16][CH2:15][CH2:14][O:13]2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 122699702-(5-Bromothiophen-2-Yl)-1,3-DioxolaneHCID 178418339Butyllithium

Product 1

HCID 23130459HCID 23130459, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-Butyl lithium (2.6N hexane solution, 15.6 mL, 39 mmol) was added dropwise to a solution of 2-(5bromo-thiophen-2-yl)-[1,3]dioxolane (7.0 g, 30 mmol) in tetrahydrofuran (40 mL) at from −75° to −68° C., and the solution was stirred for 20 minutes. 3-Chlorobenzyl bromide (4.3 mL, 33 mmol) was added dropwise to this reaction solution at from −75° C. to −68° C., and the solution was stirred for 20 minutes. The cold bath was removed, and the reaction solution was gradually allowed to room temperature. Water and ethyl acetate were added to the reaction solution, which was then partitioned, the solvent was evaporated, the residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=20:1), and the title compound (1.6 g, 5.7 mmol, 19.0%) was obtained as a yellow oil.

Workup

  1. stirringthe solution was stirred for 20 minutes
  2. customThe cold bath was removed
  3. customwas gradually allowed to room temperature
  4. additionWater and ethyl acetate were added to the reaction solution, which
  5. customwas then partitioned
  6. customthe solvent was evaporated
  7. customthe residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-3511029dee154744b335d458c115d251
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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