Nitric Acid → 2-Bromo-3-fluoro-6-nitrobenzoic acid

HRID 471606

반응식

HRID 471606 반응식
[Br:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[N+:12]([O-])([OH:14])=[O:13]>OS(O)(=O)=O>[Br:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[C:7]([N+:12]([O-:14])=[O:13])[C:3]=1[C:4]([OH:6])=[O:5]

참가 물질

4

반응물 2

HCID 944Nitric AcidHCID 3026222-Bromo-3-fluorobenzoic acid

생성물 1

HCID 598491772-Bromo-3-fluoro-6-nitrobenzoic acid수율 77%

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

반응 조건

온도
0 °C

실험 절차

In a 1 L, three necked flask fitted with a dropping funnel and a thermometer were charged 2-bromo-3-fluorobenzoic acid (Example 134 g) (28.23 g, 0.13 mol) and concentrated H2SO4 (200 mL). After cooling to 0° C., HNO3 (70%, 16.0 mL) was added dropwise over 30 min, keeping the temperature between 0 to 10° C. After 1 h, the reaction mixture was poured into the crushed ice keeping the temperature below 20° C. The mixture was extracted with EtOAc (2×200 mL), the combined extract was washed with brine and dried with MgSO4. The filtrate was evaporated to give 27.27 g (77%) of a mixture of 2-bromo-3-fluoro-6-nitrobenzoic acid and 2-bromo-3-fluoro-5-nitrobenzoic acid (1:0.4) as a brown solid. 1H NMR (400 MHz, DMSO-d6) δ 8.33 (dd, J=9.6, 4.8 Hz, 1H), 7.21 (dd, J=10.0, 8.0 Hz, 1H).

후처리

  1. customIn a 1 L, three necked flask fitted with a dropping funnel
  2. custombetween 0 to 10° C
  3. extractionThe mixture was extracted with EtOAc (2×200 mL)
  4. extractionthe combined extract
  5. washwas washed with brine
  6. dry with materialdried with MgSO4
  7. customThe filtrate was evaporated

출처 및 근거

ORD 기록
ord-3ff681a966ba4954afdbf48c5fed65a2
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633186B2

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