Boron tribromide → HCID 86687436, compound

HRID 1473393Notes

Reaction equation

HRID 1473393 reaction equation
[CH2:1]([S:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15]([Cl:19])=[N:14][CH:13]=[C:12]2[O:20]C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([S:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15]([Cl:19])=[N:14][CH:13]=[C:12]2[OH:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 86687434HCID 86687434, compound

Product 1

HCID 86687436HCID 86687436, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

6-(benzylthio)-1-chloro-4-methoxyisoquinoline (Intermediate VVV; 0.400 g, 1.267 mmol) was dissolved in DCM (12.67 ml) and cooled to 0° C. Boron tribromide (0.487 ml, 5.06 mmol) was added and the reaction was stirred for 30 minutes, then warmed to room temperature and stirred overnight. The reaction was cooled to 0° C. and carefully quenched with saturated sodium bicarbonate solution. The reaction was diluted with ethyl acetate and the layers were separated. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were dried with sodium sulfate, filtered, and concentrated to afford crude 6-(benzylthio)-1-chloroisoquinolin-4-ol as an orange solid. (ESI) 302.1 (M+H)+.

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred overnight
  3. temperatureThe reaction was cooled to 0° C.
  4. customcarefully quenched with saturated sodium bicarbonate solution
  5. additionThe reaction was diluted with ethyl acetate
  6. customthe layers were separated
  7. extractionThe aqueous layer was extracted with ethyl acetate
  8. dry with materialthe combined organic layers were dried with sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-9fd106f93ee245a7b2164d2213ab4bfe
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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