Water → 5-(1,3-Benzoxazol-2-yl)-2-hydroxy benzonitrile

HRID 7759

Reaction equation

HRID 7759 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[CH:12][C:13]([O:18]C)=[C:14]([CH:17]=1)[C:15]#[N:16].B(Br)(Br)Br.CCOC(C)=O.O>C(Cl)Cl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[CH:12][C:13]([OH:18])=[C:14]([CH:17]=1)[C:15]#[N:16]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 219909835-(1,3-Benzoxazol-2-yl)-2-methoxy benzonitrile

Product 1

HCID 1357525215-(1,3-Benzoxazol-2-yl)-2-hydroxy benzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(1,3-benzoxazol-2-yl)-2-methoxy benzonitrile (270 mg, 1.1 mmol) in CH2Cl2 (5 mL) at 0° C., was added BBr3 (1.0M solution in CH2Cl2, 430 μL, 4.4 mmol) dropwise. The reaction was stirred at it for 4 h. EtOAc (150 mL) was added, as well as H2O (30 mL). The organic layer was washed with brine (2×20 mL), dried (MgSO4), concentrated and the crude product was recrystallized in EtOAc to afford 5-(1,3-benzoxazol-2-yl)-2-hydroxy benzonitrile. MS (ESI) 237 (M+H)+.

Workup

  1. washThe organic layer was washed with brine (2×20 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customthe crude product was recrystallized in EtOAc

Sources & evidence

ORD record
ord-d520da0a211748ddab0429d699c7af31
Source dataset
uspto-grants-2006_08
Patent number
US07087601B2

Linked notes

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