Cesium carbonate → 4-Tert-butyl-2-(2-chloro-4-fluorophenoxy)benzoic acid

HRID 1625199

반응식

HRID 1625199 반응식
Br[C:2]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Cl:15][C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[OH:23].C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1>[C:11]([C:9]1[CH:8]=[CH:7][C:3]([C:4]([OH:6])=[O:5])=[C:2]([O:23][C:17]2[CH:18]=[CH:19][C:20]([F:22])=[CH:21][C:16]=2[Cl:15])[CH:10]=1)([CH3:14])([CH3:13])[CH3:12]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 748142-Chloro-4-fluorophenolHCID 2363522-Bromo-4-tert-butylbenzoic acid

생성물 1

HCID 576877084-Tert-butyl-2-(2-chloro-4-fluorophenoxy)benzoic acid수율 72.2%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
120 °C

실험 절차

In a pressure-vessel, a stirring mixture of 2-bromo-4-tert-butylbenzoic acid (1.00 g, 3.89 mmol) and 2-chloro-4-fluorophenol (860 mg, 620 μL, 5.87 mmol) in toluene (20 mL) was added Cs2CO3 (2.53 g, 7.78 mmol) followed by copper(I) triflate benzene complex (98 mg, 0.19 mmol). The sealed vessel was heated to 120° C. for 16 h. After cooling to room temperature, the reaction mixture was partitioned between 50 mL EtOAc and 50 mL H2O. The aqueous layer was acidified using 2.0 N HCl(aq) and re-extracted with EtOAc. The combined organic solution was dried over Na2SO4, filtered, and concentrated. The residue was purified via silica gel chromatography using 0-3% MeOH/CH2Cl2 to give the product, 4-tert-butyl-2-(2-chloro-4-fluorophenoxy)benzoic acid as a white solid (907 mg, 2.81 mmol) in 72% yield. LC/MS: m/z 323.2 (M+H) at 1.99 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

후처리

  1. temperatureAfter cooling to room temperature
  2. customthe reaction mixture was partitioned between 50 mL EtOAc and 50 mL H2O
  3. extractionre-extracted with EtOAc
  4. dry with materialThe combined organic solution was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified via silica gel chromatography

출처 및 근거

ORD 기록
ord-729cbca1987243dba6b471d9c68653b3
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08779197B2

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