Iodine → HCID 178505763, compound

HRID 2202124Notes

Reaction equation

HRID 2202124 reaction equation
[Zn:1].II.[Br:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1.C[Si](Cl)(C)C>O1CCCC1>[Br-:4].[F:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][Zn+:1])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 807IodineHCID 6397ChlorotrimethylsilaneHCID 23994ZincHCID 680214-Fluorobenzyl bromide2×

Product 1

HCID 178505763HCID 178505763, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred mixture of Zn metal (18.5 g, 289.06 mmol, 1.09 equiv), I2 (500 mg, 1.97 mmol, 0.01 equiv) and 1-(bromomethyl)-4-fluorobenzene (5 g, 0.10 equiv) in anhydrous tetrahydrofuran (50 mL) maintained under nitrogen at room temperature was added dropwise a solution of 1-(bromomethyl)-4-fluorobenzene (45 g, 211.6 mmol, 0.90 equiv) in tetrahydrofuran (200 mL). TMSCl (500 mg, 4.60 mmol, 0.02 equiv) was then added dropwise to the reaction. The resulting mixture was refluxed for 10 h. The solution was cooled to 0° C. and used in the next step immediately.

Workup

  1. temperatureThe resulting mixture was refluxed for 10 h
  2. temperatureThe solution was cooled to 0° C.

Sources & evidence

ORD record
ord-82d8d67e34174504a05b01a8d455fba3
Source dataset
uspto-grants-2016_06
Patent number
US09365527B2

Reaction notes

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