Ethylene Glycol → 1-(4-Bromophenyl)cyclopropane-1-carboxylic acid
Reaction equation
[OH-:1].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7](CC#N)=[CH:6][CH:5]=1.Br[CH2:14][CH2:15]Cl.[CH2:17]([OH:20])[CH2:18]O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([C:18]2([C:17]([OH:20])=[O:1])[CH2:15][CH2:14]2)=[CH:8][CH:9]=1Participants
Conditions
- Temperature
- 100 °C
Procedure
Sodium hydroxide (50% aqueous solution, 60.0 g, 1.03 mol) was added to a mixture of 4-bromobenzeneacetonitrile (19.6 g, 0.100 mol), benzyltriethylammonium chloride (1.8 g, 0.0079 mol), and 1-bromo-2-chloro-ethane (30.0 g, 0.209 mol) at 50° C. for 5 hours. 1,2-Ethanediol (200.0 mL, 3.588 mol) was added to the mixture and the resulting mixture was heated at 100° C. overnight. The mixture was poured into ice-water (30 mL) and was extracted with ethyl ether (2×10 mL). The aqueous phase was acidified (to pH=2) with 1N HCl and was extracted with ethyl acetate (4×15 mL). The combined organic phases were washed with brine (10 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was used in next step reaction without further purification.
Workup
- extractionwas extracted with ethyl ether (2×10 mL)
- extractionwas extracted with ethyl acetate (4×15 mL)
- washThe combined organic phases were washed with brine (10 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was used in next step reaction without further purification
Sources & evidence
- ORD record
- ord-2955afb7dc7f40bab3a1670978e8a772
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07776874B2
Reaction notes
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