Imidazole → tert-Butyl (4-(2-iodoethyl)phenyl)carbamate

HRID 533568Notes

Reaction equation

HRID 533568 reaction equation
O[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:6][CH:5]=1.N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:42]I>ClCCl>[I:42][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 11413715N-Boc-2-(4-aminophenyl)ethanol

Product 1

HCID 117703773tert-Butyl (4-(2-iodoethyl)phenyl)carbamateYield 86.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

tert-Butyl [4-(2-hydroxyethyl)phenyl]carbamate (6.45 g, 27.18 mmol) in dichloromethane (20 mL) was added drop-wise to a solution of imidazole (2.04 g, 30.0 mmol), triphenylphosphine (8.60 g, 32.8 mmol), and iodine (8.28 g, 32.6 mmol) in dichloromethane (80 mL) at 0° C. The reaction was allowed to warm to rt and was stirred overnight at room temperature. The reaction was cooled to 0° C. and quenched with water (100 mL). The organic layer was separated, washed with saturated aqueous sodium thiosulfate (100 mL), water (100 mL), and brine (100 mL). The organics were dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified via flash chromatography using an Analogix SF40-150 g column eluting with 30% EtOAc in heptane to afford the title compound as a white solid (8.16 g, 86.5%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.52 (s, 9H) 3.13 (t, J=8.00 Hz, 2H) 3.27-3.35 (m, 2H) 7.12 (d, J=8.59 Hz, 2H) 7.32 (d, J=8.59 Hz, 2H).

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. customquenched with water (100 mL)
  3. customThe organic layer was separated
  4. washwashed with saturated aqueous sodium thiosulfate (100 mL), water (100 mL), and brine (100 mL)
  5. dry with materialThe organics were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified via flash chromatography
  9. washeluting with 30% EtOAc in heptane

Sources & evidence

ORD record
ord-fe789aa403c441d3aa48963fa255ca7d
Source dataset
uspto-grants-2014_10
Patent number
US08853258B2

Reaction notes

Loading…