Methanol → HCID 18172482, compound

HRID 397082Notes

Reaction equation

HRID 397082 reaction equation
B(Br)(Br)Br.[F:5][C:6]([F:28])([F:27])[C:7]([N:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19]C)[CH:15]=2)[CH:10]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:8].CO>C(Cl)Cl>[F:28][C:6]([F:5])([F:27])[C:7]([N:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:19])[CH:15]=2)[CH:10]1[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:8]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 18172390HCID 18172390, compound

Product 1

HCID 18172482HCID 18172482, compoundYield 146.8%

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 2,2,2-trifluoro-1-(6-methoxy-1-phenyl-3,4-dihydro-1H-isoquinoline-2-yl)ethanone (0.172 g, 0.513 mmol) in anhydrous CH2Cl2 (10 ml) at 0° C. under N2. The resulting yellow solution was stirred at 0° C. for 30 min, then warmed to rt and stirred at rt for 22 hr. MeOH (5 ml) was slowly added to the reaction mixture with stirring and the resulting solution was concentrated in vacuo to give 0.242 g of yellow oil. Purification by flash chromatography, eluting with hexane:EtOAc (8:2) gave 0.143 g (87% yield) of white solid.

Workup

  1. temperaturewarmed to rt
  2. stirringstirred at rt for 22 hr
  3. stirringwith stirring
  4. concentrationthe resulting solution was concentrated in vacuo

Sources & evidence

ORD record
ord-551a855aa4674b06a4ea8e9c0bf81ee6
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

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