반응 #166191

반응 방정식

DMF

2-bromo-4-fluoro-benzoic acid tert-butyl ester

lithium diisopropylamide

→

title compound

수율 62.0%

2-Bromo-4-fluoro-3-formyl-benzoic acid tert-butyl ester

수율 62.0%

용매

THF

반응 조건

후처리

1. 1
   workup.STIRRINGthen stirred for a further 10 minutes
2. 2
   기타before quenching with acetic acid (3 mL)
3. 3
   기타The products were partitioned between ethyl acetate and water
4. 4
   기타the organic layer was separated
5. 5
   세척washed with brine
6. 6
   건조dried (Na2SO4)
7. 7
   여과filtered
8. 8
   농축concentrated in vacuo
9. 9
   기타to give a yellow oil which
10. 10
    기타crystallized
11. 11
    기타The crude product was triturated in cyclohexane

실험 절차

To a solution of 2-bromo-4-fluoro-benzoic acid tert-butyl ester (10.0 g, 36 mmol) in THF (100 mL) at −78° C. under an atmosphere of nitrogen was added lithium diisopropylamide (1.8M solution, 20 mL, 36 mmol) dropwise. The reaction mixture was stirred for 1.25 hours before adding DMF (10 mL) then stirred for a further 10 minutes before quenching with acetic acid (3 mL). The products were partitioned between ethyl acetate and water, the organic layer was separated, washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to give a yellow oil which crystallized on standing. The crude product was triturated in cyclohexane to give the title compound as a yellow solid (6.8 g, 62%). 1H NMR (CDCl3, 400 MHz) 10.38 (1H, s), 7.80-7.73 (1H, m), 7.17 (1H, t, J=9.09 Hz), 1.62 (9H, s).

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