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

HRID 1849746ノート

反応式

HRID 1849746 の反応式
[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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒2 回HCID 962Water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-da83b631b87e447d99a9e5edfdc89df5
出典データセット
uspto-grants-2015_02
特許番号
US08952169B2

反応ノート

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