Boron tribromide → HCID 86687792, compound

HRID 2280981Notes

Reaction equation

HRID 2280981 reaction equation
[NH2:1][C:2]1[C:7]([O:8]C)=[CH:6][C:5]([C:10]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[O:11])=[C:4]([F:18])[CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([C:10]([N:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)=[O:11])=[C:4]([F:18])[CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 71512861HCID 71512861, compound

Product 1

HCID 86687792HCID 86687792, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of (4-amino-2-fluoro-5-methoxyphenyl)(morpholino)methanone (260 mg, 1.02 mmol), BBr3 (1.28 g, 5.10 mmol), and CH2Cl2 (15 mL) was stirred at 0° C. for 2 h. The reaction was quenched by water at 0° C. The resulting mixture was extracted with EtOAc. The combined organic layer was washed with brine (20 mL), dried over sodium sulfate, and concentrated under reduced pressure. Silica-gel column chromatography afforded the title product as yellow solid (200 mg, 81%).

Workup

  1. customThe reaction was quenched by water at 0° C
  2. extractionThe resulting mixture was extracted with EtOAc
  3. washThe combined organic layer was washed with brine (20 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-717fa9d6bf0f4ab18464e10fabe91fe7
Source dataset
uspto-grants-2015_09
Patent number
US09139566B2

Reaction notes

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