Phosphorus tribromide → HCID 58083522, compound
Reaction equation
[CH:1]1([CH2:5][O:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH2:13]O)[CH2:4][CH2:3][CH2:2]1.P(Br)(Br)[Br:16].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Br:16][CH2:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[O:6][CH2:5][CH:1]1[CH2:4][CH2:3][CH2:2]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
A solution of {2-[(cyclobutylmethyl)oxy]phenyl}methanol (for a preparation see Intermediate 26) (0.5 g, 2.60 mmol) in anhydrous DCM (5 ml) was cooled to 5° C. under nitrogen. A solution of phosphorus tribromide (0.248 ml, 2.63 mmol) in anhydrous DCM (2 ml) was added dropwise. The reaction mixture was stirred allowing to warm up to ambient temperature for 1.5 h. The reaction mixture was then poured onto a mixture of ice/water (40 ml) and saturated sodium bicarbonate (15 ml). DCM (30 ml) was added and the layers were separated. The aqueous phase was extracted with DCM (20 ml). The combined DCM extracts were dried (Na2SO4) and evaporated in vacuo to give the title compound as a pale yellow oil (0.50 g); LCMS: (System 4) tRET=3.61 min, no strong MH+ or (M-H)− detected.
Workup
- temperatureto warm up to ambient temperature for 1.5 h
- customthe layers were separated
- extractionThe aqueous phase was extracted with DCM (20 ml)
- dry with materialThe combined DCM extracts were dried (Na2SO4)
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-f48e4c90eb4847369291ba7ed72b94ef
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08399436B2
Reaction notes
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