Boron tribromide → 7-Hydroxy-3-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)quinoline

HRID 1011428Notes

Reaction equation

HRID 1011428 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([C:13]3[O:14][CH2:15][C:16]([CH3:19])([CH3:18])[N:17]=3)[CH:9]=[N:10]2)=[CH:5][CH:4]=1.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([C:13]3[O:14][CH2:15][C:16]([CH3:19])([CH3:18])[N:17]=3)[CH:9]=[N:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 231597597-Methoxy-3-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)quinoline

Product 1

HCID 1356182107-Hydroxy-3-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)quinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 7-methoxy-3-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)quinoline (2.56 g, 10 mmol) prepared in stage A and BBr3 (7.41 g, 30 mmol) in dichloromethane (40 mL) are stirred for 12 hours at room temperature. The mixture was quenched with saturated sodium hydrogen carbonate. Extraction with dichloromethane, drying (MgSO4) and evaporation furnished the desired compound.

Workup

  1. customThe mixture was quenched with saturated sodium hydrogen carbonate
  2. extractionExtraction with dichloromethane
  3. customdrying
  4. custom(MgSO4) and evaporation

Sources & evidence

ORD record
ord-f08bfad8e287479db8bc5f23ab85c845
Source dataset
uspto-grants-2011_07
Patent number
US07977354B2

Reaction notes

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