Boron tribromide → 2-(4-Chloro-6-fluoroquinazolin-2-yl)phenol

HRID 2406174Notes

Reaction equation

HRID 2406174 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:12])[CH:10]=2)[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19]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]=[C:9]([F:12])[CH:10]=2)[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[OH:19])[N:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 58683904HCID 58683904, compound

Product 1

HCID 1361214352-(4-Chloro-6-fluoroquinazolin-2-yl)phenolYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-chloro-6-fluoro-2-(2-methoxyphenyl)quinazoline (3.0 g, 10.3 mmol) in CH2Cl2 (15 mL) was cooled to −78° C. Then, 1 M BBr3 (51.95 mL, 59.95 mmol) was added dropwise. The reaction was warmed to room temperature and was quenched with NaHCO3 and extracted twice with CH2Cl2. The organic layer was dried over MgSO4, filtered, and concentrated. Purification via silica gel chromatography using 5-20% CH2Cl2 in hexanes gave 2-(4-chloro-6-fluoroquinazolin-2-yl)phenol (1.61 g, 57%). LC/MS: m/z 275.1 (M+H)+ at 3.8 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customwas quenched with NaHCO3
  2. extractionextracted twice with CH2Cl2
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification via silica gel chromatography

Sources & evidence

ORD record
ord-aef6ccf53f4740c2b8e8262a74a6ae03
Source dataset
uspto-grants-2014_08
Patent number
US08809353B2

Reaction notes

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