Iodine → 1-Bromo-3-Iodo-2-hydroxymethyl naphthalene

HRID 580915Notes

Reaction equation

HRID 580915 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH2:12][OH:13].[I:14]I>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([I:14])[C:3]=1[CH2:12][OH:13]

Participants

4

Reactant 2

HCID 807IodineHCID 13113200(1-Bromonaphthalen-2-yl)methanol

Product 1

HCID 543721211-Bromo-3-Iodo-2-hydroxymethyl naphthaleneYield 26.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A suspension of thalium trifluoro acetate (1.37 g, 2.53 mmole) in anhydrous CCl4 containing 24 (0.5 g, 2.1095 mmole) was refluxed under argon. Iodine (0.535 g, 2.1095 mmole) was added dropwise in a solution of CCl4 (10 ml). The mixture was refluxed for another 60 min. The reaction was cooled and quenched with 10% solution of sodium thiosulfate and then extracted with 3×50 ml of methylene chloride. The combined methylene chloride fractions were thoroughly washed several times with H2O, brine, dried with anhydrous magnesium sulfate, and evaporated in vacuo to give a dark brown thick oil. The crude dark brown oil was purified by chromatography (hexane/ ethyl acetate; 80:20) to afford 0.2 g of 25 (7%) as a light cream solid. A single component was detected by TLC (hexane/ethyl acetate; 80:20) Rf, 0.5; NMR (CDCl3). δ4.8-5 (2H, d, CH2 --OH), d 7.4-8.4 (m, 5H, naphthyl). MS (HRFAB) (M+Li)+ calcd for C11H8OBrI, 368.8963 found 368.8978.

Workup

  1. temperaturewas refluxed under argon
  2. temperatureThe mixture was refluxed for another 60 min
  3. temperatureThe reaction was cooled
  4. customquenched with 10% solution of sodium thiosulfate
  5. extractionextracted with 3×50 ml of methylene chloride
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customevaporated in vacuo
  8. customto give a dark brown thick oil
  9. customThe crude dark brown oil was purified by chromatography (hexane/ ethyl acetate; 80:20)

Sources & evidence

ORD record
ord-6b18c4e60fca4117b03bd7d53cda753e
Source dataset
uspto-grants-1999_07
Patent number
US05919797

Reaction notes

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