Benzyl Bromide → (S)-2-methyl-3-bromo-1-benzyloxypropane
Reaction equation
[CH3:1][C@H:2]([CH2:5][Br:6])[CH2:3][OH:4].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>>[CH3:1][C@H:2]([CH2:5][Br:6])[CH2:3][O:4][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1Participants
Procedure
The starting material, 3-(2-(2-(nonafluorobutoxy)tetrafluoroethoxy)-2,2-difluoroethoxy))-(R)-2-fluoropropyloxy)-(R)-2-methylpropane-1-methanesulfonate, was prepared as follows: (S)-2-methyl-3-bromopropanol was alkylated with benzyl bromide to produce (S)-2-methyl-3-bromo-1-benzyloxypropane, which was then combined with 3-(2-(2-(nonafluorobutoxy)tetrafluoroethoxy)-2,2-difluoroethoxy))-(R)-2-fluoropropanol, followed by hydrogenation with 10% Pd/C to remove the benzyl protecting group. The title compound was prepared by combining 5-hexyloxy-2-(4-hydroxyphenyl)pyrimidine (0.7 g, 2.58 mmol) and 3-(2-(2-(nonafluorobutoxy)tetrafluoroethoxy)-2,2-difluoroethoxy))-(R)-2-fluoropropyloxy)-(R)-2-methylpropane-1-methanesulfonate (1.7 g, 2.58 mmol) essentially as described in Example 8 of International Patent Publication No. WO 96/33251. The resulting crude product was further purified by chromatography eluting with 10:1 hexanes/ethyl acetate, and was recrystallized from heptane, followed by Kugelrohr distillation (b.p. 180-190° C. at 0.02 torr; yield 1.28 g).
Sources & evidence
- ORD record
- ord-da62b90b70714101b5a4a7b5e0def86c
- Source dataset
- uspto-grants-2000_02
- Patent number
- US06030547
Reaction notes
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