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

HRID 2062147Notes

Reaction equation

HRID 2062147 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>C(Cl)Cl>[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)phenolYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-chloro-2-(2-methoxyphenyl)quinazoline (1.0 g, 3.7 mmol) in 40 mL CH2Cl2 at −78° C. was added 5 equivalents of 1 M BBr3 dropwise. After complete addition the cooling bath was removed and the reaction was quenched with NaHCO3 after 90 minutes. The product was extracted twice with CH2Cl2, dried over Na2SO4, filtered, and concentrated. Purification via silica gel chromatography using 60:40 CH2Cl2: hexanes gave 2-(4-chloroquinazolin-2-yl)phenol (700 mg, 74%). LC/MS: m/z 257.1 (M+H)+ at 3.75 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)). 1H NMR (400 MHz, DMSO-d6) δ 8.44 (m, 1H), 8.24 (m, 3H), 7.89 (m, 1H), 7.49 (m, 1H), 7.05 (m, 2H).

Workup

  1. additionAfter complete addition the cooling bath
  2. customwas removed
  3. customthe reaction was quenched with NaHCO3 after 90 minutes
  4. extractionThe product was extracted twice with CH2Cl2
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification via silica gel chromatography

Sources & evidence

ORD record
ord-0088301503ad4fe3b3caebef29e2d957
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

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