Hydrochloric Acid → 2-Azido-4-bromobenzoic acid

HRID 270680

반응식

HRID 270680 반응식
[NH2:1][C:2]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl.N([O-])=O.[Na+].[N-:17]=[N+:18]=[N-].[Na+].CC([O-])=O.[Na+]>O>[N:1]([C:2]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])=[N+:17]=[N-:18]

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 886912-Amino-4-bromobenzoic acidHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

생성물 1

HCID 860515482-Azido-4-bromobenzoic acid수율 68%

시약·촉매·용매 1

HCID 962Water용매3회

실험 절차

To a solution of 2-amino-4-bromobenzoic acid (8.4 g, 0.039 mol) in a mixture of concentrated HCl (70 mL) and H2O (100 mL) was added a solution of NaNO2 (2.8 g, 0.044 mol) in H2O (40 mL) such that the reaction temperature did not rise above 5° C. After addition was complete the resulting slurry was stirred for 15 min and the cold mixture added in aliquots to a solution of NaN3 (2.5 g, 0.039 mol) and NaOAc (38 g, 0.47 mol) in H2O (80 mL) at room temperature. The resulting slurry was stirred for 30 min and the solid collected by filtration giving 6.4 g (68% yield) of product as a tan powder. 1H NMR (360 MHz, DMSO): 7.46 (1H, dd, J 1.4 and 7.5 Hz), 7.57 (1H, d, J 1.4 Hz), 7.70 (1H, d, J 7.5 Hz).

후처리

  1. customdid not rise above 5° C
  2. additionAfter addition
  3. stirringThe resulting slurry was stirred for 30 min
  4. filtrationthe solid collected by filtration

출처 및 근거

ORD 기록
ord-70be7ff4632b4714a00d4f6df4eb851d
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449585B2

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