Dimethylformamide → tert-Butyl 5-bromo-2-chlorobenzoate

HRID 561779노트

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HRID 561779 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].CN(C=O)C.C(Cl)(=O)C(Cl)=O.[CH3:23][C:24]([CH3:27])([O-])[CH3:25].[K+]>C1(C)C=CC=CC=1.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7]([O:9][C:24]([CH3:27])([CH3:25])[CH3:23])=[O:8]

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 331275-Bromo-2-chlorobenzoic acidHCID 65578Oxalyl chlorideHCID 23665647Potassium tert-butoxide

생성물 1

HCID 22291846tert-Butyl 5-bromo-2-chlorobenzoate

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

실험 절차

5-bromo-2-chlorobenzoic acid (1 eq.) and anhydrous DMF (1.2 eq.) was taken up in toluene (0.9 M). To this was then added, dropwise over 5 min, oxalyl chloride (1.2 eq.) and the reaction mixture was stirred at RT for 1 h. The volatiles were then removed in vacuo and the resulting residue was taken up in toluene (0.9 M). At 0° C., potassium tert-butoxide (2.5 eq.) was added and the reaction mixture was stirred at RT for 1 h. The reaction mixture was poured into H2O and extracted with ether. The combined organic extracts were washed with brine, dried over MgSO4 and filtered. Concentration of the filtrate in vacuo afforded a pale yellow oil. Purification of the crude product thus obtained by way of flash chromatography (SiO2, Hex→85:15 (v/v) Hex:EtOAc) afforded the title compound as a light yellow oil.

후처리

  1. additionTo this was then added, dropwise over 5 min
  2. customThe volatiles were then removed in vacuo
  3. extractionextracted with ether
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customConcentration of the filtrate in vacuo afforded a pale yellow oil
  8. customPurification of the crude product
  9. customthus obtained by way of flash chromatography (SiO2, Hex→85:15 (v/v) Hex:EtOAc)

출처 및 근거

ORD 기록
ord-f24f1e28b8144ab2b52b5569db03e2ef
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063105B2

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