1-(Chloromethyl)-4-iodobenzene → HCID 17755957, compound

HRID 73133Notes

Reaction equation

HRID 73133 reaction equation
[I:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Cl)=[CH:4][CH:3]=1.[C:10]1(=[O:20])[NH:14][C:13](=[O:15])[C:12]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:11]12.[K]>CN(C=O)C>[I:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:14]2[C:13](=[O:15])[C:12]3=[CH:16][CH:17]=[CH:18][CH:19]=[C:11]3[C:10]2=[O:20])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8172111-(Chloromethyl)-4-iodobenzeneHCID 24194345Phthalimide potassium salt

Product 1

HCID 17755957HCID 17755957, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

(Brown, Stephen; Grigg, Ronald; Hinsley, Joanne; Korn, Stewart; Sridharan, Visuvanathar; Uttley, Michael; Tetrahedron (2001), 57(52), 10347-10355.) A mixture of 4-iodobenzylchloride (40.0 g, 134.7 mmol), potassium phthalimide (26.20 g, 141.5 mmol) and dry DMF (150 mL) was heated overnight at 55° C. under Ar, and then the solvent was removed at reduced pressure. The solid residue was triturated with CHCl3 (200 mL), filtered, and washed with CHCl3 (3×200 mL). The combined organic extracts were successively washed with aqueous 0.2 M NaOH (200 mL) and H2O (400 mL), and then dried (MgSO4). The solvent was removed at reduced pressure to afford a crude solid, which was triturated with Et2O to obtain a white solid (37.00 g, 75%): Rf=0.75 (1/1 EtOAc/hexanes); mp 138-139° C.; 1H NMR (CDCl3) 4.77 (s, CH2), 7.17 (d, J=8.6 Hz, 2 ArH), 7.63 (d, J=8.6 Hz, 2 ArH), 7.78 (dd, J=3.0, 5.7 Hz, 2 PhtH), 7.83 (dd, J=3.0, 5.7 Hz, 2 PhtH); 13C NMR (CDCl3) 41.0 (CH2), 93.5 (Cl), 123.4, 130.6, 131.9, 134.1, 135.9, 137.7 (6 Ar), 167.2 (2C(O)); HRMS (ESI) 363.9831 [M+H+] (calcd for C17H13NO2H+ 363.9835).

Workup

  1. customthe solvent was removed at reduced pressure
  2. customThe solid residue was triturated with CHCl3 (200 mL)
  3. filtrationfiltered
  4. washwashed with CHCl3 (3×200 mL)
  5. washThe combined organic extracts were successively washed with aqueous 0.2 M NaOH (200 mL) and H2O (400 mL)
  6. dry with materialdried (MgSO4)
  7. customThe solvent was removed at reduced pressure
  8. customto afford a crude solid, which
  9. customwas triturated with Et2O

Sources & evidence

ORD record
ord-39d20c6d378e4d6b87c835284ed659a9
Source dataset
uspto-grants-2014_09
Patent number
US08829033B2

Reaction notes

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