Methanol → Methyl 4-bromo-3-(trifluoromethyl)benzoate

HRID 400764노트

반응식

HRID 400764 반응식
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].S(Cl)(Cl)=O.[CH3:19]O>>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:19])=[O:7])=[CH:4][C:3]=1[C:11]([F:12])([F:13])[F:14]

참가 물질

4

반응물 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 247213904-Bromo-3-(trifluoromethyl)benzoic acid

생성물 1

HCID 10891333Methyl 4-bromo-3-(trifluoromethyl)benzoate수율 94%

실험 절차

To a suspension of 4-bromo-3-(trifluoromethyl)benzoic acid (Acceledev 000625, 15 g; 55.76 mmol) in MeOH (300 mL) at RT was added dropwise thionyl chloride (16.18 mL; 223.04 mmol) over 15 min. The reaction mixture was stirred at RT for 12 hours. The solvent was concentrated and the crude residue was diluted with EtOAc (500 mL). The organic layer was washed with a saturated aqueous solution of NaHCO3 (200 mL), water (200 mL), brine (200 mL), dried over MgSO4 and concentrated affording the title compound as an orange solid (14.80 g, 94%). 1H NMR (DMSO-d6, 300 MHz) δ 8.26 (m, 1H), 8.14-8.13 (m, 2H), 3.93 (s, 3H). HPLC (Method A) Rt 4.71 min (Purity: 99.0%).

후처리

  1. concentrationThe solvent was concentrated
  2. additionthe crude residue was diluted with EtOAc (500 mL)
  3. washThe organic layer was washed with a saturated aqueous solution of NaHCO3 (200 mL), water (200 mL), brine (200 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ba49ed2eb09245c3903991461fb0327d
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741923B2

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