Boron Trichloride → HCID 86612907, compound

HRID 915880Notes

Reaction equation

HRID 915880 reaction equation
[Cl:1][C:2]1[C:3]2[C:17]([I:18])=[CH:16][N:15]([C@@H:19]3[O:34][C@H:33]([CH2:35][O:36]CC4C=CC(Cl)=CC=4Cl)[C@@H:22]([O:23]CC4C=CC(Cl)=CC=4Cl)[C@@:20]3([CH3:46])[OH:21])[C:4]=2[N:5]=[C:6]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[N:7]=1.B(Cl)(Cl)Cl>C(Cl)Cl>[Cl:1][C:2]1[C:3]2[C:17]([I:18])=[CH:16][N:15]([C@@H:19]3[O:34][C@H:33]([CH2:35][OH:36])[C@@H:22]([OH:23])[C@@:20]3([CH3:46])[OH:21])[C:4]=2[N:5]=[C:6]([NH:8][C:9](=[O:14])[C:10]([CH3:12])([CH3:13])[CH3:11])[N:7]=1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 131726594HCID 131726594, compound

Product 1

HCID 86612907HCID 86612907, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-72.5 °C

Procedure

To a solution of compound 15.2 (7.03 g, 8.43 mmol) in CH2Cl2 (200 mL) at −75° C. was added boron trichloride (1M in CH2Cl2; 83.4 mL, 83.4 mmol). The mixture was stirred at −75 to −70° C. for 2 hr and then at −30 to −20° C. for 3 hr. The reaction was quenched by addition of MeOH/CH2Cl2 (1/1, 9 mL) and the resulting mixture stirred at −20 to −15° C. for 30 min., then neutralized with aq. ammonia (28%, 35 mL) at 0° C. and stirred at room temperature for 10 min. The solid which separated was filtered and washed with MeOH/CH2Cl2 (1/1, 500 mL). The combined filtrates were evaporated and the residue was purified on a silica gel column using CH2Cl2/MeOH (50/1, 40/1) as the eluents to furnish the target compound 15.3 as an off-white solid (2.93 g, 80%).

Workup

  1. waitat −30 to −20° C. for 3 hr
  2. customThe reaction was quenched by addition of MeOH/CH2Cl2 (1/1, 9 mL)
  3. stirringthe resulting mixture stirred at −20 to −15° C. for 30 min.
  4. customneutralized with aq. ammonia (28%, 35 mL) at 0° C.
  5. stirringstirred at room temperature for 10 min
  6. customThe solid which separated
  7. filtrationwas filtered
  8. washwashed with MeOH/CH2Cl2 (1/1, 500 mL)
  9. customThe combined filtrates were evaporated
  10. customthe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-25b89760056744c3b04246844e5b78eb
Source dataset
uspto-grants-2007_09
Patent number
US07268119B2

Reaction notes

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