Boron tribromide → 6-Hydroxy-1-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)naphthalen-2-yl trifluoromethanesulfonate

HRID 445218Notes

Reaction equation

HRID 445218 reaction equation
B(Br)(Br)Br.Cl.[F:6][C:7]([F:41])([F:40])[S:8]([O:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:22]C)[CH:18]=2)[C:13]=1[O:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][N:34]2[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]2)=[CH:27][CH:26]=1)(=[O:10])=[O:9]>ClCCl>[F:40][C:7]([F:6])([F:41])[S:8]([O:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([OH:22])[CH:18]=2)[C:13]=1[O:24][C:25]1[CH:26]=[CH:27][C:28]([O:31][CH2:32][CH2:33][N:34]2[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]2)=[CH:29][CH:30]=1)(=[O:10])=[O:9]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 866551546-Methoxy-1-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)naphthalen-2-yl trifluoromethanesulfonate hydrochloride

Product 1

HCID 866071646-Hydroxy-1-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)naphthalen-2-yl trifluoromethanesulfonateYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Add a solution of boron tribromide in dichloromethane (4 M, 5 mL, 20.00 mmol) to a solution of 6-methoxy-1-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)naphthalen-2-yl trifluoromethanesulfonate hydrochloride (2.8 g, 4.98 mmol) and dichloromethane (100 ml). Stir the reaction for 2 hours and then quench with aqueous sodium bicarbonate. Extract the mixture 3 times with dichloromethane. Combine the extracts, dry over sodium sulfate, filter and concentrate to obtain the title compound (2.4 g, 4.68 mmol).

Workup

  1. customthe reaction for 2 hours
  2. customquench with aqueous sodium bicarbonate
  3. extractionExtract the mixture 3 times with dichloromethane
  4. dry with materialdry over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-cd011b2c98ef476d84713ce7e823f4c9
Source dataset
uspto-grants-2013_07
Patent number
US08476300B2

Reaction notes

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