Boron Trichloride → HCID 136008554, compound

HRID 2216514Notes

Reaction equation

HRID 2216514 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[N:18]=[C:17](/[CH:26]=[C:27](\[CH3:33])/[C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.B(Cl)(Cl)Cl>C(Cl)Cl>[CH:20]1([N:19]2[C:15]([C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=3)=[CH:16][C:17](/[CH:26]=[C:27](\[CH3:33])/[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[N:18]2)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 11155006HCID 11155006, compound

Product 1

HCID 136008554HCID 136008554, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-50 °C

Procedure

To a solution 4.1 (83 mg, 0.187 mmol) in CH2Cl2 (2 ml) at −50° C. was added a 1M solution of BCl3 in CH2Cl2 (933 μL, 0.933 mmol) followed by stirring at −50° C. for 15 min, and quenched with MeOH. The mixture was diluted with EtOAc, washed with H2O, sat. NaHCO3, brine, and dried (Na2SO4). Filtration through a 1″ pad of SiO2 and concentration to provided 4.3, 67 mg (100%). MS (ESI) 355.3 (MH+), 353.3 (MH−).

Workup

  1. customquenched with MeOH
  2. additionThe mixture was diluted with EtOAc
  3. washwashed with H2O, sat. NaHCO3, brine
  4. dry with materialdried (Na2SO4)
  5. filtrationFiltration through a 1″
  6. concentrationpad of SiO2 and concentration
  7. customto provided 4.3, 67 mg (100%)

Sources & evidence

ORD record
ord-f65b86afc05041c2b1ccb32dca7b3c0c
Source dataset
uspto-grants-2006_09
Patent number
US07112601B2

Reaction notes

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