Iodine → HCID 178443584, compound

HRID 531207Notes

Reaction equation

HRID 531207 reaction equation
[Zn:1].[Cl-].[Li+].II.[CH2:6]([CH:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:13][Br:14])[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]>C1COCC1>[Br-:14].[CH2:6]([CH:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:13][Zn+:1])[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 4

HCID 807IodineHCID 23994Zinc3×HCID 433294Lithium ChlorideHCID 3793645HCID 3793645, compound

Product 1

HCID 178443584HCID 178443584, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of zinc dust (1.91 g, 29.9 mmol) and lithium chloride (1.35 g, 31.8 mmol) was heated strongly under vacuum for about 10 minutes. After cooling to room temperature, the flask was filled with nitrogen and iodine (0.294 g, 1.16 mmol) added. The solid mixture was stirred for 5 minutes before the addition of dry THF (20 mL). The slurry was heated to 90° C. and then 2-hexyl-1-bromooctane added in a single portion (5.0 g, 18 mmol) with the progress of zinc insertion monitored by GC-MS of a quenched aliquot. After approximately 48 hours heating, zinc insertion was shown to be approximately 95% complete.

Workup

  1. temperaturewas heated strongly under vacuum for about 10 minutes
  2. additionadded
  3. temperatureThe slurry was heated to 90° C.
  4. temperatureAfter approximately 48 hours heating

Sources & evidence

ORD record
ord-c970bc2b1586441084a962006c4763eb
Source dataset
uspto-grants-2016_05
Patent number
US09353130B2

Reaction notes

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