Boron tribromide → HCID 136121322, compound

HRID 2062222Notes

Reaction equation

HRID 2062222 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[C:17]([O:18]C)=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:20])[N:3]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:20][C:13]1[C:12]([C:4]2[N:3]=[C:2]([Cl:1])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)=[C:17]([OH:18])[CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 58010939HCID 58010939, compound

Product 1

HCID 136121322HCID 136121322, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-chloro-2-(2-chloro-6-methoxyphenyl)quinazoline (300 mg, 0.98 mmol) in 10 mL CH2Cl2 was added dropwise 5 equivalents of a 1 M BBr3 solution in CH2Cl2 at −78° C. The reaction was warmed to room temperature and was complete in 30 minutes. The reaction was quenched With a saturated aqueous NaHCO3 solution to pH 7. The aqueous layer was extracted with CH2Cl2, and the combined extracts were dried over Na2SO4, filtered, and concentrated to obtain 3-chloro-2-(4-chloroquinazolin-2-yl)phenol. LC/MS: m/z 291.3 (M+H)+ at 3.16 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customThe reaction was quenched With a saturated aqueous NaHCO3 solution to pH 7
  2. extractionThe aqueous layer was extracted with CH2Cl2
  3. dry with materialthe combined extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-432e867e99c64b66aa363154a9682b9d
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

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