Boron Trichloride → HCID 57999459, compound

HRID 511988Notes

Reaction equation

HRID 511988 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[CH:7][CH:6]=[C:5]([O:15]C)[C:4]=1[C:17]1[CH:22]=[CH:21][C:20]([C:23](=[O:28])[C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=1.B(Cl)(Cl)Cl>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].C(Cl)Cl>[F:25][C:24]([F:26])([F:27])[C:23]([C:20]1[CH:19]=[CH:18][C:17]([C:4]2[C:5]([OH:15])=[CH:6][CH:7]=[C:8]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C:3]=2[O:2][CH3:1])=[CH:22][CH:21]=1)=[O:28]

Participants

5

Reactant 2

HCID 25135Boron TrichlorideHCID 44128292HCID 44128292, compound

Product 1

HCID 57999459HCID 57999459, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Compound 39.3 (1 equiv.) and n-Bu4NI (3 equiv.) were stirred in dry CH2Cl2 at −78° C. under nitrogen. A solution of BCl3 (3.2 mL, using 1M solution in CH2Cl2) was added over 2 min period. After 5 min, the solution was warmed to 0° C. and stirring was continued for 2 h. The reaction was quenched with ice-water, the resulting mixture was stirred for 30 min, and partially concentrated to remove CH2Cl2. Water was added and the mixture was extracted with diethyl ether. The combined organic layer was washed with saturated aqueous NaCl solution, dried over MgSO4, and evaporated. Purification by flash column chromatography on silica gel (18% acetone in hexane) gave the product 40.3 in 68% yield (270 mg).

Workup

  1. waitwas continued for 2 h
  2. customThe reaction was quenched with ice-water
  3. stirringthe resulting mixture was stirred for 30 min
  4. concentrationpartially concentrated
  5. customto remove CH2Cl2
  6. additionWater was added
  7. extractionthe mixture was extracted with diethyl ether
  8. washThe combined organic layer was washed with saturated aqueous NaCl solution
  9. dry with materialdried over MgSO4
  10. customevaporated
  11. customPurification by flash column chromatography on silica gel (18% acetone in hexane)

Sources & evidence

ORD record
ord-3665b8a6e0c4473786ea7c9d42231ea0
Source dataset
uspto-grants-2015_08
Patent number
US09102622B2

Reaction notes

Loading…