Boron tribromide → HCID 10491161, compound

HRID 418863Notes

Reaction equation

HRID 418863 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][C:11]3[C:16]([C:17](=[O:19])[CH:18]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][C:11]3[C:16]([C:17](=[O:19])[CH:18]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 2324877HCID 2324877, compound

Product 1

HCID 10491161HCID 10491161, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In a 50 mL round-bottomed flask fitted with condenser and magnetic stirrer, 2-(4-methoxyphenyl)-thiochromen-4-one (500 mg, 1.86 mmol) and DCM (20 mL) were taken. The mixture was cooled to 0° C. and BBr3 (933 mg, 3.72 mmol, 1M solution in DCM) was added slowly at 0° C. Then the reaction mixture was stirred for overnight at rt under N2. The unreacted BBr3 was carefully quenched by addition of MeOH under cooling. Solvent was removed under reduced pressure to give crude product, which was purified by column chromatography using 5% MeOH in DCM to afford 2-(4-hydroxy-phenyl)-thiochromen-4-one (380 mg, 80%). MS (ES) m/z: 255.02 (M+1).

Workup

  1. customIn a 50 mL round-bottomed flask fitted with condenser and magnetic stirrer
  2. customThe unreacted BBr3 was carefully quenched by addition of MeOH
  3. temperatureunder cooling
  4. customSolvent was removed under reduced pressure
  5. customto give crude product, which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-7c20c6da67d64354b98cdc61b4d57488
Source dataset
uspto-grants-2012_01
Patent number
US08093273B2

Reaction notes

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