Boron tribromide → HCID 136121322, compound

HRID 2062265Notes

Reaction equation

HRID 2062265 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, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-chloro-2-(2-chloro-6-methoxyphenyl)quinazoline (0.3 g, 0.98 mmol) in CH2Cl2 at −78° C. was added 5 equivalents of 1 M BBr3 solution (4.9 mL, 4.9 mmol) in CH2Cl2. The reaction was complete after 30 minutes After allowing it to warm to room temperature, the reaction mixture was quenched with aqueous NaHCO3 to pH 7, the layers were separated and the aqueous layer was extracted with CH2Cl2. The combined organic extracts were dried over MgSO4, filtered, and concentrated. Purification via silica gel chromatography using 2:1 CH2Cl2:hexanes yielded 3-chloro-2-(4-chloroquinazolin-2-yl)phenol (0.17 g, 60%). LC/MS: m/z 291.1 (M+H)+ at 3.16 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA))

Workup

  1. customthe reaction mixture was quenched with aqueous NaHCO3 to pH 7
  2. customthe layers were separated
  3. extractionthe aqueous layer was extracted with CH2Cl2
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification via silica gel chromatography

Sources & evidence

ORD record
ord-e1186a542d0c4a52924a3a196b1ef11c
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

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