2-(Bromomethyl)-1-chloro-4-iodobenzene → HCID 11372903, compound

HRID 1169875Notes

Reaction equation

HRID 1169875 reaction equation
Br[CH2:2][C:3]1[CH:8]=[C:7]([I:9])[CH:6]=[CH:5][C:4]=1[Cl:10].[C:11]1(=[O:21])[NH:15][C:14](=[O:16])[C:13]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:12]12.[K]>CN(C=O)C>[Cl:10][C:4]1[CH:5]=[CH:6][C:7]([I:9])=[CH:8][C:3]=1[CH2:2][N:15]1[C:14](=[O:16])[C:13]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:12]2[C:11]1=[O:21]

Participants

4

Reactant 2

HCID 117390382-(Bromomethyl)-1-chloro-4-iodobenzeneHCID 24194345Phthalimide potassium salt

Product 1

HCID 11372903HCID 11372903, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Bromomethyl-2-chloro-5-iodo-benzene (60) (400 mg, 1.2 mmol) and potassium phthalimide (693 mg, 1.5 mmol) were stirred in dry DMF (20 mL) and heated to 80° C. for 3 hours. After cooling, the suspension was filtered and concentrated in vacuo, and the residue was partitioned between water (30 mL) and Et2O (30 mL). The aqueous phase was extracted with ether (20 mL×3). The combined organic phases were dried over Na2SO4, filtered and concentrated to give 63 (455 mg, 95%). 1H NMR (CDCl3, 300 MHz) δ 7.92-7.86 (m, 2H), 7.78-7.75 (m, 2H), 7.54-7:50 (m, 2H), 7.10 (d, J=8.4 Hz, 1H), 4.93 (s, 2H). MS (m/e) (API-ES) 397.9 (M)+, m.p. 134-136° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe suspension was filtered
  3. concentrationconcentrated in vacuo
  4. customthe residue was partitioned between water (30 mL) and Et2O (30 mL)
  5. extractionThe aqueous phase was extracted with ether (20 mL×3)
  6. dry with materialThe combined organic phases were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-814f4c5b19404e3bb24dee380aad07ac
Source dataset
uspto-grants-2010_11
Patent number
US07825126B2

Reaction notes

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