2-Bromopropane → HCID 14940155, compound
Reaction equation
[C:1](=O)([S:3][CH2:4][P:5]([O:11][CH:12]([CH3:14])[CH3:13])([O:7][CH:8]([CH3:10])[CH3:9])=[O:6])[CH3:2].C[O-].[Na+].Br[CH:20](C)C>CO>[CH:1]([S:3][CH2:4][P:5](=[O:6])([O:11][CH:12]([CH3:14])[CH3:13])[O:7][CH:8]([CH3:10])[CH3:9])([CH3:20])[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To a stirred solution of S-(diisopropoxyphosphoryl)methyl ethanethioate (1.00 g, 3.93 mmol; Example 206, Step A) in methanol (39.3 mL) at 0° C. was added sodium methoxide (7.87 mL, 3.93 mmol), followed by 2-bromopropane (0.44 mL, 4.72 mmol). The reaction was stirred at 25° C. for 16 hours. The reaction solvent was removed in vacuo and the crude material was partitioned between water and EtOAc (2×) and the layers were separated. The aqueous layer was extracted with EtOAc and the combined organic layers were dried over Na2SO4, filtered and the filtrate was concentrated under reduced pressure. Purification of the residue by flash chromatography on silica gel (40 g column, eluent: 0 to 75% DCM/hexanes) provided the title compound as an off-white solid.
Workup
- customThe reaction solvent was removed in vacuo
- customthe crude material was partitioned between water and EtOAc (2×)
- customthe layers were separated
- extractionThe aqueous layer was extracted with EtOAc
- dry with materialthe combined organic layers were dried over Na2SO4
- filtrationfiltered
- concentrationthe filtrate was concentrated under reduced pressure
- customPurification of the residue by flash chromatography on silica gel (40 g column, eluent: 0 to 75% DCM/hexanes)
Sources & evidence
- ORD record
- ord-73adac52f6c1422ea111cc5a7faa00d6
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09296736B2
Reaction notes
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