Boron tribromide → HCID 67004256, compound

HRID 1513950Notes

Reaction equation

HRID 1513950 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[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].B(Br)(Br)Br.C(Cl)(Cl)Cl.C(O)(C)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[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[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]2)=[CH:25][CH:24]=1)=[O:22]

Participants

6

Reactant 4

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 21906603Chloroform isopropyl alcoholHCID 57552529HCID 57552529, compound

Product 1

HCID 67004256HCID 67004256, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve [2-(2,6-difluorophenyl)-6-methoxy-naphthalen-1-yl]-[4-(2-piperidin-1-ylethoxy)-phenyl]-methanone (1.5 g, 3.0 mmol) in 500 mL methylene chloride and chill in ice. To this solution add boron tribromide (6.0 mL, 63 mmol) in portions with swirling between additions. Allow to come to room temperature and stir for one hour. Pour into a two-phase system consisting of an organic layer of 3/1 chloroform/isopropanol and an aqueous layer of saturated sodium bicarbonate. Separate the phases and dry the organic layer using 3 Å molecular sieves. Purify on a silica column eluting with a 0-10% methanol/methylene chloride gradient to give 600 mg (44%) of the title compound.

Workup

  1. temperaturechill in ice
  2. customto come to room temperature
  3. additionPour into a two-phase system
  4. customSeparate the phases
  5. customdry the organic layer
  6. customPurify on a silica column
  7. washeluting with a 0-10% methanol/methylene chloride gradient

Sources & evidence

ORD record
ord-581027e05a164c378b5d6f2b43c9b744
Source dataset
uspto-grants-2012_07
Patent number
US08217032B2

Reaction notes

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