Boron tribromide → HCID 58466135, compound
Reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][C:8]([O:16]C)=[CH:9][CH:10]=3)[C:5]3([CH2:21][O:20][C:19]([NH2:22])=[N:18]3)[C:4]=2[C:3]=1[F:23].B(Br)(Br)Br>C(Cl)Cl>[NH2:22][C:19]1[O:20][CH2:21][C:5]2([N:18]=1)[C:4]1[C:3]([F:23])=[C:2]([Br:1])[CH:15]=[CH:14][C:13]=1[O:12][C:11]1[C:6]2=[CH:7][C:8]([OH:16])=[CH:9][CH:10]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 2′-bromo-1′-fluoro-7′-methoxy-5H-spiro[oxazole-4,9′-xanthen]-2-amine (0.575 g, 1.516 mmol) in 15 mL of CH2Cl2 at −15° C. was added boron tribromide (1.0 M in CH2Cl2, 4.55 mL, 4.55 mmol). The mixture was slowly allowed to warm to 0° C. over the course of 1.25 hours at which point the reaction was carefully quenched with 2 mL of MeOH and saturated sodium bicarbonate (100 mL). This mixture was poured into a separatory funnel containing EtOAc (100 mL). The layers were separated and the aqueous layer was extracted with EtOAc (2×100 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to provide 2-amino-2′-bromo-1′-fluoro-5H-spiro[oxazole-4,9′-xanthen]-7′-ol as a glassy red solid. MS m/z=365.1 [M+H].
Workup
- customwas carefully quenched with 2 mL of MeOH and saturated sodium bicarbonate (100 mL)
- additionThis mixture was poured into a separatory funnel
- additioncontaining EtOAc (100 mL)
- customThe layers were separated
- extractionthe aqueous layer was extracted with EtOAc (2×100 mL)
- washThe combined organic layers were washed with brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-1cb1d0bdfeb8429f849515853cb48c3b
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08883782B2
Reaction notes
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