Carbon Dioxide → HCID 17902884, 화합물

HRID 1820962

반응식

HRID 1820962 반응식
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8](Br)=[CH:7][C:6]=1[F:12])([CH3:3])[CH3:2].C([Li])CCC.[C:18](=[O:20])=[O:19]>C1COCC1.CCCCCCC>[F:12][C:6]1[CH:7]=[C:8]([CH:9]=[CH:10][C:5]=1[O:4][CH:1]([CH3:3])[CH3:2])[C:18]([OH:20])=[O:19]

참가 물질

6

반응물 3

HCID 280Carbon DioxideHCID 27733894-Bromo-2-fluoro-1-isopropoxybenzeneHCID 178418339Butyllithium

생성물 1

HCID 17902884HCID 17902884, 화합물수율 70%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8900Heptane용매

반응 조건

온도
-78 °C

실험 절차

A solution of 639 mg (2.74 mmol) 1-isopropyloxy-2-fluoro-4-bromobenzene (from Step A) in 10 mL of THF at −78° C. was treated with 1.64 mL of 2.0 M n-butyllithium in heptane. After stirring at −78° C. for 30 min, the mixture was poured onto 300 g of crushed dry ice and allowed to warm up to rt. The mixture was partitioned between 100 mL of 2.0 N NaOH and 100 mL of Et2O. The aqueous layer was separated, acidified using 5.0 N HCl to pH 2, and extracted with CH2Cl2 (3×50 mL). The organic layers were combined, dried over MgSO4, and concentrated to afford 380 mg of the title compound: 1H NMR (500 MHz, CDCl3) δ 1.41 (d, J=6.2, 6H), 4.65-4.73 (m, 1H), 7.00 (t, J=8.5, 1H), 7.79-7.87 (m, 2H).

후처리

  1. temperatureto warm up to rt
  2. customThe mixture was partitioned between 100 mL of 2.0 N NaOH and 100 mL of Et2O
  3. customThe aqueous layer was separated
  4. extractionextracted with CH2Cl2 (3×50 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-598d1b05263743d3a98ab5309914f5a0
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07605171B2

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