Boron tribromide → 4-Chloro-2-hydroxybenzamide

HRID 453116Notes

Reaction equation

HRID 453116 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[C:4]([O:11]C)[CH:3]=1.B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[C:4]([OH:11])[CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 19741766HCID 19741766, compound

Product 1

HCID 137262814-Chloro-2-hydroxybenzamideYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-chloro-2-methoxybenzamide (0.74 g, 3.99 mmol) in dichloromethane (50 ml) was cooled to −78° C. followed by addition of BBr3 (1.15 ml, 11.96 mmol) under nitrogen atmosphere. The reaction mixture was allowed to stir at room temperature for 2 h. After the completion of reaction (TLC monitoring), the solution was cooled to 0° C. and quenched with water. The resulting solution was basified by aqueous NaHCO3 and extracted with EtOAc (3×100 ml). The combined organics was dried over anhydrous Na2SO4, filtered and concentrated to get the desired product (0.608 g, 89%). MS: 172.33 (M+H)+.

Workup

  1. customAfter the completion of reaction (TLC monitoring)
  2. temperaturethe solution was cooled to 0° C.
  3. customquenched with water
  4. extractionextracted with EtOAc (3×100 ml)
  5. dry with materialThe combined organics was dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c3198b94586846e1b2b985583f7ddd94
Source dataset
uspto-grants-2013_07
Patent number
US08492414B2

Reaction notes

Loading…