4-Bromobenzyl bromide → Ethyl 1-(4-bromobenzyl)cyclobutanecarboxylate
Reaction equation
[Li+].CC([N-]C(C)C)C.[CH:9]1([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:12][CH2:11][CH2:10]1.[Br:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Br)=[CH:21][CH:20]=1>C1COCC1>[Br:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][C:9]2([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:12][CH2:11][CH2:10]2)=[CH:21][CH:20]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -40 °C
Procedure
To a solution of LDA (1.2 eq) in THF at −78° C. was added ethyl cyclobutanecarboxylate (1 eq) and reaction mixture was warmed up to −40° C. for 10 min. The reaction was cooled back to −78° C. for 1 h, then 4-bromobenzyl bromide (1.1 eq) was added as a solid to the mixture. The reaction mixture was warmed to 0° C. in an ice bath. The reaction was quenched with a saturated solution of NH4Cl and extract 3× with ethyl acetate, dried with MgSO4 and evaporated to dryness. Flash chromatography with 95:5 hexanes:ethyl acetate afforded ethyl 1-(4-bromobenzyl)cyclobutanecarboxylate.
Workup
- temperatureThe reaction was cooled back to −78° C. for 1 h
- temperatureThe reaction mixture was warmed to 0° C. in an ice bath
- customThe reaction was quenched with a saturated solution of NH4Cl
- extractionextract 3× with ethyl acetate
- dry with materialdried with MgSO4
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-f4c41caf8621402b9a45ec89ad0905ec
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07238706B2
Reaction notes
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