Hydrochloric Acid → [2-(2,4-Difluoro-phenyl)-6-hydroxy-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone

HRID 1513946Notes

Reaction equation

HRID 1513946 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19]C)[CH:15]=2)[C:10]=1[C:21]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][N:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)=[CH:25][CH:24]=1)=[O:22].Cl.CCOCC.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:19])[CH:15]=2)[C:10]=1[C:21]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][N:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)=[CH:25][CH:24]=1)=[O:22]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 57552512[2-(2,4-Difluoro-phenyl)-6-methoxynaphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone

Product 1

HCID 67004951[2-(2,4-Difluoro-phenyl)-6-hydroxy-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanoneYield 100.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve [2-(2,4-difluoro-phenyl)-6-methoxynaphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone (10.8 g, 21.5 mmol) in methylene chloride (200 mL). Add 2M HCl in ether (21.5 mL, 43 mmol) and concentrate in vacuo. Redissolve the foam in methylene chloride (200 mL) and cool to 0° C. under nitrogen. Slowly add boron tribromide (10.1 mL, 107 mmol) and stir at 0° C. for 30 minutes. Slowly pour into saturated aqueous sodium bicarbonate and extract with 20% WA in chloroform. Dry the organic layer with sodium sulfate, filter and concentrate in vacuo to yield 10.5 g (100%) of the title compound.

Workup

  1. concentrationconcentrate in vacuo
  2. dissolutionRedissolve the foam in methylene chloride (200 mL)
  3. extractionextract with 20%
  4. dry with materialDry the organic layer with sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-9c6d6b2ced72480bbbdaa1ea7f71ac39
Source dataset
uspto-grants-2012_07
Patent number
US08217032B2

Reaction notes

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