4-Methyl-3-(trifluoromethyl)benzoic acid → 4-(Bromomethyl)-3-(trifluoromethyl)benzoic acid

HRID 1184845

반응식

HRID 1184845 반응식
[Br:1]([O-])(=O)=O.[Na+].[CH3:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:8]=1[C:16]([F:19])([F:18])[F:17].S(=O)(O)[O-].[Na+]>O.C(OCC)(=O)C.CCOCC>[Br:1][CH2:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:8]=1[C:16]([F:17])([F:18])[F:19]

참가 물질

7

반응물 3

HCID 27755924-Methyl-3-(trifluoromethyl)benzoic acidHCID 23665763Sodium BisulfiteHCID 23668195Sodium Bromate

생성물 1

HCID 231458934-(Bromomethyl)-3-(trifluoromethyl)benzoic acid수율 81.2%

시약·촉매·용매 3

HCID 962Water용매2회HCID 3283Diethyl Ether용매HCID 8857Ethyl Acetate용매

반응 조건

온도
50 °C

실험 절차

To a solution of sodium bromate (1109 mg, 7.35 mmol) in H2O (3.3 mL) was added 4-methyl-3-trifluoromethyl-benzoic acid (500 mg, 2.449 mmol) in ethyl acetate (5 mL), followed by a solution of sodium bisulfite (765 mg, 7.35 mmol) in H2O (9 mL) over a period of about 15 min. The mixture was stirred overnight at room temperature and overnight at 50° C. The mixture was poured in ether (50 mL). The aqueous layer was extracted twice with ether and the combined organic layer was washed with anhydrous Na2S2O3 solution, dried, filtered and concentrated in vacuo to give the crude 4-(bromomethyl)-3-(trifluoromethyl)benzoic acid 35 (563 mg, 81%) which was used without further purification. (m/z)=282 and 284 (M+H)+.

후처리

  1. extractionThe aqueous layer was extracted twice with ether
  2. washthe combined organic layer was washed with anhydrous Na2S2O3 solution
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-17e57dc3f99f4701b61acd8c4b8203f1
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08669256B2

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