Dichloromethane → HCID 68864367, compound

HRID 2109402Notes

Reaction equation

HRID 2109402 reaction equation
B(Br)(Br)Br.[F:5][C:6]1[CH:7]=[C:8]([CH:32]=[CH:33][C:34]=1[O:35]C)[C:9]([NH:11][NH:12][C:13]([C:15]1[O:16][CH:17]=[C:18]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:19]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:14])=[O:10].ClCCl>O>[F:5][C:6]1[CH:7]=[C:8]([CH:32]=[CH:33][C:34]=1[OH:35])[C:9]([NH:11][NH:12][C:13]([C:15]1[O:16][CH:17]=[C:18]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:19]=1[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:14])=[O:10]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 68864000HCID 68864000, compound

Product 1

HCID 68864367HCID 68864367, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

Boron tribromide (1 M dichloromethane solution: 6.00 ml) was added dropwise to a mixture of the compound of Example 31 (0.86 g) and dichloromethane (20 ml) at 0° C., and the mixture was stirred at 25° C. overnight. Water was added to the reaction solution. The thus-precipitated crystals were collected by filtration, purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/3), and recrystallized from ethanol, thereby giving 0.64 g of the desired compound. Melting point: 243-245° C.

Workup

  1. filtrationThe thus-precipitated crystals were collected by filtration
  2. custompurified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/3)
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-8a64ae8b162f431c80977dbbd6bb271b
Source dataset
uspto-grants-2009_04
Patent number
US07514452B2

Reaction notes

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