Boron tribromide → 6-[(2-chloro-4-hydroxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-4-methyl-4H-benzo[1,4]oxazin-3-one

HRID 2386752Notes

Reaction equation

HRID 2386752 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8]C)[CH:5]=[CH:4][C:3]=1[CH:10]([CH3:29])[C:11]([C:17]1[CH:18]=[CH:19][C:20]2[O:25][CH2:24][C:23](=[O:26])[N:22]([CH3:27])[C:21]=2[CH:28]=1)([OH:16])[C:12]([F:15])([F:14])[F:13].B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH:10]([CH3:29])[C:11]([C:17]1[CH:18]=[CH:19][C:20]2[O:25][CH2:24][C:23](=[O:26])[N:22]([CH3:27])[C:21]=2[CH:28]=1)([OH:16])[C:12]([F:13])([F:14])[F:15]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 666972506-[2-(2-Chloro-4-methoxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-4-methyl-4H-benzo[1,4]oxazin-3-one

Product 1

HCID 666972396-[(2-chloro-4-hydroxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-4-methyl-4H-benzo[1,4]oxazin-3-oneYield 103.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-70 °C

Procedure

A solution of 6-[2-(2-chloro-4-methoxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-4-methyl-4H-benzo[1,4]oxazin-3-one (4.9 g, 11.4 mmol) in dichloromethane (130 ml) was cooled to −70° C. A 1 M solution of boron tribromide in dichloromethane (45.6 ml) was added dropwise (25 min) and the mixture was stirred at −70° C. for 1.5 h. The ice bath was removed and the mixture was stirred at r.t. for 3 h. The reaction mixture was poured on a mixture of ice water and sat aq NaHCO3 solution, extracted three times with dichloromethane. The organic phases were washed with water and dried (MgSO4) and concentrated. The product was dried under high vacuum to give the title compound (4.9 g) as an off-white solid. MS (m/e)=416.1 [M+H+].

Workup

  1. customThe ice bath was removed
  2. stirringthe mixture was stirred at r.t. for 3 h
  3. additionThe reaction mixture was poured on a mixture of ice water
  4. extractionextracted three times with dichloromethane
  5. washThe organic phases were washed with water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe product was dried under high vacuum

Sources & evidence

ORD record
ord-90942cf8938b473fab1dbe02f7bf0287
Source dataset
uspto-grants-2012_09
Patent number
US08268820B2

Reaction notes

Loading…