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

HRID 533498Notes

Reaction equation

HRID 533498 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9]O)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:30]I>ClCCl.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 95.5%

Reagents, catalysts & solvents 2

HCID 795ImidazoleCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(4-bromophenyl)ethanol (40.0 g, 0.199 mol) in dichloromethane (10 mL) was added dropwise to a solution of imidazole (22.4 mg, 0.329 mmol), triphenylphosphine (66.5 g, 0.254 mol), and iodine (65.0 g, 0.26 mol) in dichloromethane (50 mL) at 0° C. When the addition was complete it was warmed to rt. After 1 hour the reaction was filtered through celite, the filtrate was washed with saturated aqueous sodium thiosufate (2×100 mL), brine (100 mL), dried over MgSO4, filtered and concentrated in vacuo. Purification by flash column chromatography on silica gel (heptane/ethyl acetate 4:1) afforded the title compound as a yellow-white solid (59.09 g, 60%). 1HNMR (400 MHz, CHLOROFORM-d) δ ppm 3.14 (t, J=7.69 Hz, 2H) 3.33 (t, J=7.69 Hz, 2H) 7.08 (d, J=7.89 Hz, 2H) 7.45 (d, J=8.31 Hz, 2H)

Workup

  1. additionWhen the addition
  2. filtrationAfter 1 hour the reaction was filtered through celite
  3. washthe filtrate was washed with saturated aqueous sodium thiosufate (2×100 mL), brine (100 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash column chromatography on silica gel (heptane/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-646373582ffc4edfa85f894137775051
Source dataset
uspto-grants-2014_10
Patent number
US08853258B2

Reaction notes

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