Reaction equation
P(Br)(Br)[Br:2].[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([O:15][CH3:16])[CH:14]=1)[CH2:10]O>C1COCC1>[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([O:15][CH3:16])[CH:14]=1)[CH2:10][Br:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Phosphorus tribromide (0.4 eq) was added to the alcohol 304 (25 g, 0.13 mol) in THF (100 mL) very slowly at −10° C. and the mixture which resulted was stirred for 15-30 min at the same temperature. By this time all the starting material had disappeared (TLC). The reaction mixture was quenched by addition of ice-cold H2O (100 mL) and then filtered through a Buchner funnel. The filtrate was diluted with brine (100 mL) and extracted with EtOAc (3×300 mL). The combined organic extracts were dried (Na2SO4) and concentrated in vacuo. The crude oil was purified by FCC (20% ethylacetate in hexane) to afford the bromide 305 as a white solid (92%)a: 1H NMR (500 MHz, CDCl3) δ 6.61 (2H, d, J=2.3 Hz), 6.46 (1H, t, J=2.3 Hz), 4.5 (2H, s), 3.85 (6H, s). 13C NMR (125 MHz, CDCl3): δ 161.3, 140.2, 107.4, 101.0, 55.8, 34.1. The spectral data for 305 were in excellent accord with data previously reported on it (Seidel et al., 1990)1. This material was employed directly in the next step.
Workup
- customthe mixture which resulted
- customThe reaction mixture was quenched by addition of ice-cold H2O (100 mL)
- filtrationfiltered through a Buchner funnel
- additionThe filtrate was diluted with brine (100 mL)
- extractionextracted with EtOAc (3×300 mL)
- dry with materialThe combined organic extracts were dried (Na2SO4)
- concentrationconcentrated in vacuo
- customThe crude oil was purified by FCC (20% ethylacetate in hexane)
Sources & evidence
- ORD record
- ord-984ac72a3a6a4f0299bfd004c79eac98
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08530512B2
Linked notes
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