Iodine → 1-Bromo-4-(2-iodoethyl)benzene

HRID 1477247Notes

Reaction equation

HRID 1477247 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9]O)=[CH:4][CH:3]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[I:30]I>C(Cl)Cl.N1C=CN=C1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][I:30])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 807IodineHCID 11776TriphenylphosphineHCID 728512-(4-Bromophenyl)ethanol

Product 1

HCID 197022221-Bromo-4-(2-iodoethyl)benzeneYield 73%

Reagents, catalysts & solvents 2

HCID 795ImidazoleCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(4-bromophenyl)ethanol (20.0 g, 100 mol) in CH2Cl2 (10 mL) was added dropwise to a solution of imidazole (22.4 mg, 0.33 mmol), PPh3 (33.3 g, 127 mmol), and I2 (32.5 g, 130 mmol) in CH2Cl2 (50 mL) at 0° C., and the reaction was warmed to room temperature and stirred overnight. The reaction mixture was washed with saturated aqueous sodium thiosulfate (2×50 mL), brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give a crude, which was purified by flash chromatography (silica gel/PE) to yield 1-bromo-4-(2-iodoethyl)benzene (9.2, 22.7 g, 73%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 3.13 (t, J=7.6 Hz, 2H), 3.32 (t, J=7.6 Hz, 2H), 7.07 (d, J=8.0 Hz, 2H), 7.44 (d, J=8.2 Hz, 2H).

Workup

  1. washThe reaction mixture was washed with saturated aqueous sodium thiosulfate (2×50 mL), brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto give a crude, which
  6. customwas purified by flash chromatography (silica gel/PE)

Sources & evidence

ORD record
ord-6fe857d8dddc400181dc70cbe60033b0
Source dataset
uspto-grants-2016_08
Patent number
US09403758B2

Reaction notes

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