Hydrochloric Acid → HCID 66995362, compound
Reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[CH:3]=1.[Mg].II.[Cl:13][CH2:14][C:15]([CH2:17][Cl:18])=[O:16].Cl>O1CCCC1>[Cl:13][CH2:14][C:15]([C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[CH:3]=1)([OH:16])[CH2:17][Cl:18]Participants
Procedure
A mixture of 1-bromo-3,5-difluorobenzene (5.0 g, 25.9 mmol), magnesium turnings (0.82 g, 31.1 mmol) and a small piece of iodine in dry tetrahydrofuran (50 mL) under nitrogen was stirred for 1 h at ambient temperature after which a solution of 1,3-dichloroacetone (3.46 g, 25.9 mmol) in dry tetrahydrofuran (20 mL) was added dropwise. The resulting mixture was stirred at ambient temperature for 1 h. Aqueous hydrochloric acid (50 ml, 5%) was added and the phases were separated and the aqueous phase was extracted with ethylacetate (2×50 ml). The combined organic phase was washed with brine, dried (Na2SO4), filtered and evaporated to dryness. The crude product was purified by flash column chromatography on silica gel (ethylacetate/isooctane, 1:9 to 1:1) to give the title compound (2.78 g, 45%). MS m/z (rel. intensity, 70 eV) 241 (M+, 1), 193 (32), 191 (bp), 127 (68), 77 (39).
Workup
- additionwas added dropwise
- customthe phases were separated
- extractionthe aqueous phase was extracted with ethylacetate (2×50 ml)
- washThe combined organic phase was washed with brine
- dry with materialdried (Na2SO4)
- filtrationfiltered
- customevaporated to dryness
- customThe crude product was purified by flash column chromatography on silica gel (ethylacetate/isooctane, 1:9 to 1:1)
Sources & evidence
- ORD record
- ord-ba23ae4ef5f94e50ab4373bd312d0dd5
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08586572B2
Reaction notes
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