Boron tribromide → HCID 11952978, compound

HRID 499757Notes

Reaction equation

HRID 499757 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([NH:11][NH:12][C:13](=[O:25])[C:14]2[C:19]([O:20]C)=[CH:18][C:17]([O:22]C)=[CH:16][C:15]=2[Cl:24])=[O:10])[CH:5]=[CH:6][CH:7]=1.B(Br)(Br)Br>ClCCl>[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([NH:11][NH:12][C:13](=[O:25])[C:14]2[C:19]([OH:20])=[CH:18][C:17]([OH:22])=[CH:16][C:15]=2[Cl:24])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 57480138HCID 57480138, compound

Product 1

HCID 11952978HCID 11952978, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.2 9 g of “69a” are suspended in 30 ml of dichloromethane. 40 ml of BBr3 are added dropwise with ice-cooling. After 48 hours at room temperature, 200 ml of ice-water are stirred in. The mixture is subjected to conventional work-up, separated over silica gel by means of a CombiFlash COMPANION instrument and crystallised from diethyl ether, giving 3.3 g of N′-[2-(3-hydroxyphenyl)acetyl]-2-chloro-4,6-dihydroxybenzohydrazide (“70”), m.p. 217°

Workup

  1. temperaturecooling
  2. customseparated over silica gel by means of a CombiFlash COMPANION instrument
  3. customcrystallised from diethyl ether

Sources & evidence

ORD record
ord-85e4fa22671446ec8e3775044fe670bf
Source dataset
uspto-grants-2010_08
Patent number
US07767716B2

Reaction notes

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