Boron Trichloride → 4-(5-(3-Chloro-4-propoxyphenyl)-1,2,4-oxadiazol-3-yl)-2-iodophenol

HRID 717690Notes

Reaction equation

HRID 717690 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23]C(C)C)=[C:19]([I:27])[CH:18]=3)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][CH3:11].B(Cl)(Cl)Cl>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([I:27])[CH:18]=3)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 666149435-(3-Chloro-4-propoxyphenyl)-3-(3-iodo-4-isopropoxyphenyl)-1,2,4-oxadiazole

Product 1

HCID 1363599364-(5-(3-Chloro-4-propoxyphenyl)-1,2,4-oxadiazol-3-yl)-2-iodophenolYield 79.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of the product of Step B (0.2 g, 0.4 mmol) in anhydrous CH2Cl2 (2 ml) 1 M BCl3 in CH2Cl2 (3 ml) was added drop wise at rt. After 1 h, more of 1M BCl3 in CH2Cl2 (1 ml) was added and this was stirred for 1 h. The reaction mixture was quenched with saturated NH4Cl solution and extracted with CH2Cl2 (20 ml). The organic layer was separated, dried over MgSO4 and filtered. The filtrates was evaporated to dryness and the residue was crystallized from MeOH to give the title compound (0.145 g, 79%), as colourless solid. 1H-NMR (CDCl3) 8.47 (d, 1H, J=1.95 Hz); 8.21 (d, 1H, J=2.1 Hz); 8.06-8.04 (m, 1H); 8.03-8.02 (m, 1H); 7.07 (d, 1H, J=8.49 Hz); 7.00 (d, 1H, J=8.7 Hz); 4.08 (t, 2H, J=6.45 Hz); 1.94-1.87 (m, 2H); 1.09 (t, 3H, J=7.44 Hz).

Workup

  1. customThe reaction mixture was quenched with saturated NH4Cl solution
  2. extractionextracted with CH2Cl2 (20 ml)
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe filtrates was evaporated to dryness
  7. customthe residue was crystallized from MeOH

Sources & evidence

ORD record
ord-d56033ec9dca4d329c8a52ae9fac4e39
Source dataset
uspto-grants-2015_11
Patent number
US09193716B2

Reaction notes

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