Methanol → HCID 67126081, compound

HRID 514056Notes

Reaction equation

HRID 514056 reaction equation
B(Br)(Br)Br.[Br:5][C:6]1[C:15]([CH3:16])=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:17]C)[CH:12]=2)[C:7]=1[C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1.CO>C(Cl)Cl>[Br:5][C:6]1[C:7]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)=[C:8]2[C:13](=[CH:14][C:15]=1[CH3:16])[CH:12]=[C:11]([OH:17])[CH:10]=[CH:9]2

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 67126222HCID 67126222, compound2×

Product 1

HCID 67126081HCID 67126081, compoundYield 4,664.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

A vessel was charged with boron tribromide (1 M in DCM, 0.7 mL, 0.7 mmol) and cooled to −78° C. 2-bromo-1-(4-chlorophenyl)-6-methoxy-3-methylnaphthalene (0.1 g, 0.28 mmol) was added as a solution in DCM (0.5 mL). The reaction was allowed to slowly warm to room temperature over 3.5 h. This procedure was repeated twice on a scale of 1 g and 4.1 g of 2-bromo-1-(4-chlorophenyl)-6-methoxy-3-methylnaphthalene with appropriate adjustments in the scale of other reagents. The three lots were combined, cooled to 0° C. and the volume of the reaction was slowly doubled with MeOH. After warming to room temperature, the mixture was concentrated in vacuo and the residue was taken up in EtOAc (150 mL), treated with saturated NaHCO3 (150 mL) and then small portions of solid NaHCO3 until the solution was pH ˜7. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organics were washed with brine, dried over anhydrous MgSO4, and concentrated in vacuo. The resulting residue was purified by Yamazen column chromatography (5-25% EtOAc/Hex) to afford 4.54 g (91%) of the title compound as a colorless syrup. LCMS-ESI+ (m/z): [M+H]+ calcd for C17H13BrClO: 348.64; found: 348.79.

Workup

  1. temperatureto slowly warm to room temperature over 3.5 h
  2. temperaturecooled to 0° C.
  3. temperatureAfter warming to room temperature
  4. concentrationthe mixture was concentrated in vacuo
  5. additiontreated with saturated NaHCO3 (150 mL)
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted with EtOAc
  8. washThe combined organics were washed with brine
  9. dry with materialdried over anhydrous MgSO4
  10. concentrationconcentrated in vacuo
  11. customThe resulting residue was purified by Yamazen column chromatography (5-25% EtOAc/Hex)

Sources & evidence

ORD record
ord-b056221896354083900b8bec787462d1
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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