Methanol → HCID 18172432, compound

HRID 397081Notes

Reaction equation

HRID 397081 reaction equation
B(Br)(Br)Br.[CH:5]1([CH:11]2[C:20]3[C:15](=[CH:16][C:17]([O:21]C)=[CH:18][CH:19]=3)[CH2:14][CH2:13][N:12]2[C:23](=[O:28])[C:24]([F:27])([F:26])[F:25])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.CO>C(Cl)Cl>[CH:5]1([CH:11]2[C:20]3[C:15](=[CH:16][C:17]([OH:21])=[CH:18][CH:19]=3)[CH2:14][CH2:13][N:12]2[C:23](=[O:28])[C:24]([F:25])([F:26])[F:27])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 18172402HCID 18172402, compound

Product 1

HCID 18172432HCID 18172432, compoundYield 113.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A 1M solution of BBr3 in CH2Cl2 (0.77 ml, 0.77 mmol) was added slowly to a solution of 1-(1-cyclohexyl-6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl)-2,2,2-trifluoroethanone (0.176 g, 0.52 mmol) in anhydrous CH2Cl2 (10 ml) at 0° C. under N2. The reaction mixture was stirred at 0° C. for 30 min, then warmed to rt and stirred at rt for 21 hr. MeOH (10 ml) was slowly added with stirring and the resulting solution was concentrated in vacuo to a orange oil. Purification by flash chromatography, eluting with hexane:EtOAc (8:2) gave 0.193 g (100% yield) of white solid.

Workup

  1. temperaturewarmed to rt
  2. stirringstirred at rt for 21 hr
  3. stirringwith stirring
  4. concentrationthe resulting solution was concentrated in vacuo to a orange oil
  5. customPurification by flash chromatography
  6. washeluting with hexane:EtOAc (8:2)

Sources & evidence

ORD record
ord-923e606444624327a89c2cb0c3c633ff
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

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