Hydrochloric Acid → 4-(Adamantan-1-ylmethoxy)-5-bromo-2-fluorobenzoic acid

HRID 1849746노트

반응식

HRID 1849746 반응식
[C:1]12([CH2:11][OH:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.CC(C)([O-])C.[K+].[Br:19][C:20]1[C:21](F)=[CH:22][C:23]([F:29])=[C:24]([CH:28]=1)[C:25]([OH:27])=[O:26].Cl.BrC1C(F)=CC=C(C=1)C(O)=O>CS(C)=O.O>[C:1]12([CH2:11][O:12][C:21]3[C:20]([Br:19])=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[C:23]([F:29])[CH:22]=3)[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 64556Tricyclo(3.3.1.1'3,7)dec-1-ylmethanolHCID 705093-Bromo-4-fluorobenzoic acidHCID 111607285-Bromo-2,4-difluorobenzoic acidHCID 23665647Potassium tert-butoxide

생성물 1

HCID 867036284-(Adamantan-1-ylmethoxy)-5-bromo-2-fluorobenzoic acid

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매2회HCID 962Water용매

실험 절차

A mixture of adamantan-1-ylmethanol (3.51 g, 21.10 mmol) and potassium tert-butoxide (5.45 g, 48.5 mmol) in anhydrous dimethylsulfoxide (125 mL) was stirred for 20 minutes. To the reaction mixture was then added 5-bromo-2,4-difluorobenzoic acid (5.00 g, 21.10 mmol) followed by anhydrous dimethylsulfoxide (25 mL). The resulting mixture was stirred for 18 hours at ambient temperature. The reaction mixture was diluted with water (300 mL), and adjusted to pH 3 with 3 M hydrochloric acid. The obtained solid was filtered off and rinsed with water (200 mL) to provide a 2:1 mixture of the title compound and 2-adamantan-1-ylmethoxy)-5-bromo-4-fluorobenzoic acid (6.97 g, 86%). Major isomer: 1H NMR (300 MHz, DMSO-d6) δ 7.94 (d, J=7.9 Hz, 1H), 7.05 (d, J=12.9 Hz, 1H), 3.65 (s, 2H), 1.98-1.83 (m, 3H), 1.72-1.48 (m, 12H); MS (ES−) m/z 381.13, 383.12 (M−1).

후처리

  1. stirringThe resulting mixture was stirred for 18 hours at ambient temperature
  2. filtrationThe obtained solid was filtered off
  3. washrinsed with water (200 mL)
  4. customto provide

출처 및 근거

ORD 기록
ord-da83b631b87e447d99a9e5edfdc89df5
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952169B2

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