Boron tribromide → 2-(6-Bromo-4-chloroquinazolin-2-yl)phenol

HRID 2062210Notes

Reaction equation

HRID 2062210 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18]C)[N:6]=[C:5]2[Cl:20].B(Br)(Br)Br>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[OH:18])[N:6]=[C:5]2[Cl:20]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 580109046-Bromo-4-chloro-2-(2-methoxyphenyl)quinazoline

Product 1

HCID 1361215002-(6-Bromo-4-chloroquinazolin-2-yl)phenolYield 111.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 6-bromo-4-chloro-2-(2-methoxyphenyl)quinazoline (0.14 g, 0.4 mmol) in CH2Cl2 (mL) was cooled in a dry ice/acetone bath. A solution of 1.0 M BBr3 in CH2Cl2 (1.2 mL, 1.2 mmol) was slowly added. The cooling bath was removed, and the reaction was stirred at room temperature for 2 h. The reaction was diluted with CH2Cl2 and made basic with a saturated NaHCO3 solution. The organic layer was separated, washed with water, dried over Na2SO4, and evaporated to give 6-bromo-4-chloro-2-(2-hydroxyphenyl)quinazoline (0.15 g).

Workup

  1. customThe cooling bath was removed
  2. additionThe reaction was diluted with CH2Cl2
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-6a64e7a498724e9785b8de89c2252d50
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

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