Boron tribromide → HCID 18963878, compound

HRID 2226958Notes

Reaction equation

HRID 2226958 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[S:11](=[O:13])(=[O:12])[N:10]([CH2:14][CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:9][CH2:8][C:7]=2[CH:23]=1.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[S:11](=[O:13])(=[O:12])[N:10]([CH2:14][CH2:15][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:9][CH2:8][C:7]=2[CH:23]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 18963881HCID 18963881, compound

Product 1

HCID 18963878HCID 18963878, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Methoxy-2-(3-phenylpropyl)-3,4-dihydro-2H-1,2-benzothiazine-1,1-dioxide (1.2 g, 4 mmol) is dissolved in CH2Cl2 (200 mL) and the resulting solution is cooled to -78°. Boron tribromide (1.1 mL, 12 mmol) is then added and the reaction is allowed to come to ambient temperature. After 12 hours the mixture is cooled to 0° and subsequently neutralized with saturated NaHCO3 solution (100 mL). The aqueous phase is then extracted with CH2Cl2 (1×100 mL). The combined organics are washed with saturated NaCl solution (2×200 mL), dried over Na2SO4 and concentrated in vacuo to give 6-hydroxy-2-(3-phenylpropyl)-3,4-dihydro-2H-1,2-benzothiazine-1,1-dioxide.

Workup

  1. temperaturethe resulting solution is cooled to -78°
  2. customto come to ambient temperature
  3. temperatureAfter 12 hours the mixture is cooled to 0°
  4. extractionThe aqueous phase is then extracted with CH2Cl2 (1×100 mL)
  5. washThe combined organics are washed with saturated NaCl solution (2×200 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-767a4486da7b49028a475e23a267576e
Source dataset
uspto-grants-1994_09
Patent number
US05350761

Reaction notes

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