Boron tribromide → 2-(4-Chloroquinazolin-2-yl)phenol

HRID 2189214Notes

Reaction equation

HRID 2189214 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18]C)[N:3]=1.B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[OH:18])[N:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 180716414-Chloro-2-(2-methoxyphenyl)quinazoline

Product 1

HCID 40509562-(4-Chloroquinazolin-2-yl)phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-chloro-2-(2-methoxyphenyl)quinazoline (0.106 g, 0.396 mmol) in dichloromethane (4.0 mL) was treated with 1 M boron tribromide in dichloromethane (4.0 mL, 3.960 mmol) at room temperature. After 18 hours, the reaction was quenched by pouring onto ice/water (100 mL) and the aqueous phase was extracted with ethyl acetate (3×100 mL). The combined organic extracts were dried (MgSO4) and the filtrate was concentrated in vacuo. The residue was used without further purification.

Workup

  1. customthe reaction was quenched
  2. additionby pouring onto ice/water (100 mL)
  3. extractionthe aqueous phase was extracted with ethyl acetate (3×100 mL)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe residue was used without further purification

Sources & evidence

ORD record
ord-10471a04ff994b079a627d162d80c792
Source dataset
uspto-grants-2012_12
Patent number
US08324226B2

Reaction notes

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