Allyl bromide → Methyl 2-allyloxy-5-methoxybenzoate

HRID 501727

반응식

HRID 501727 반응식
FC(F)(F)C(N[C@@H:6]1[C:14]2C(=CC=C(OC)C=2)C(=O)[CH2:7]1)=O.[CH3:20][O:21][C:22]1[CH:31]=[C:26]([C:27]([O:29][CH3:30])=[O:28])[C:25]([OH:32])=[CH:24][CH:23]=1.C(Br)C=C.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH2:14]([O:32][C:25]1[CH:24]=[CH:23][C:22]([O:21][CH3:20])=[CH:31][C:26]=1[C:27]([O:29][CH3:30])=[O:28])[CH:6]=[CH2:7]

참가 물질

6

반응물 4

HCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 1472787(S)-2,2,2-trifluoro-N-(6-methoxy-3-oxo-2,3-dihydro-1H-inden-1-yl)acetamideHCID 4072341Methyl 2-hydroxy-5-methoxybenzoate

생성물 1

HCID 59560455Methyl 2-allyloxy-5-methoxybenzoate수율 100%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Step AS (1). A mixture of 10 g (55 mmol) of methyl 5-methoxysalicylate, 9.3 mL (110 mMol) of allyl bromide and 36 g (110 mmol) of cesium carbonate in 100 mL of acetonitrile was stirred at rt for 2 h. The reaction was filtered to remove cesium carbonate and concentrated under vacuum to yield 13.3 g (100%) of methyl 2-allyloxy-5-methoxybenzoate as a yellowish solid, which was used directly in the next reaction without purification. LC-MS (M+H)+=223; 1H NMR (400 MHz, CDCl3) δ ppm 3.77 (s, 3H) 3.88 (s, 3H) 4.49-4.58 (m, 2H) 5.20-5.29 (m, 1H) 5.39-5.50 (m, 1H) 5.96-6.11 (m, 1H) 6.89 (d, J=9.06 Hz, 1H) 6.98 (dd, J=9.07, 3.27 Hz, 1H) 7.32 (d, J=3.02 Hz, 1H).

후처리

  1. filtrationThe reaction was filtered
  2. customto remove cesium carbonate
  3. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-fd18380c1d674437ad5ac44a1a8269e4
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772221B2

연결된 노트

불러오는 중…