Boron tribromide → HCID 23043622, compound

HRID 2165097Notes

Reaction equation

HRID 2165097 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23]C)=[C:19]([O:25]C)[CH:18]=3)=[CH:11][CH:10]=2)=[O:7])=[C:4]([OH:29])[CH:3]=1.B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([OH:25])[CH:18]=3)=[CH:11][CH:10]=2)=[O:7])=[C:4]([OH:29])[CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 23043625HCID 23043625, compound

Product 1

HCID 23043622HCID 23043622, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

A dichloromethane (40 ml) solution of 4-chloro-N-[4-[2-(3,4-dimethoxyphenyl)ethyl]phenyl]-2-hydroxybenzamide (0.50 g, 1.21 mmol) is cooled to -78° C. under an argon atmosphere. Boron tribromide (1.0M solution in dichloromethane, 5.5 ml, 5.5 mmol) is added, and the mixture is stirred at -78° C. for four hours, followed by stirring at ambient temperature for two hours. The solution is then recooled to -20° C. and quenched with water (5.5 ml). The mixture is allowed to stir at ambient temperature for 12 hours, after which additional water (10 ml) is added. Filtration affords 4-chloro-N-[4-[2-(3,4-dihydroxyphenyl)ethyl]phenyl]-2-hydroxybenzamide (0.42 g, 91%), mp 229°-213° C. after recrystallization from methanol/water.

Workup

  1. stirringby stirring at ambient temperature for two hours
  2. customis then recooled to -20° C.
  3. customquenched with water (5.5 ml)
  4. stirringto stir at ambient temperature for 12 hours
  5. additionafter which additional water (10 ml) is added
  6. filtrationFiltration

Sources & evidence

ORD record
ord-f25f8386d43c439a9aa1568fffac9c6c
Source dataset
uspto-grants-1990_07
Patent number
US04939133

Reaction notes

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