Acetic Acid → HCID 19361673, compound

HRID 376260Notes

Reaction equation

HRID 376260 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3[O:16][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=4)=[CH:18][CH:19]=3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.BrBr.[C:28]([OH:31])(=[O:30])[CH3:29]>>[C:28]([O:31][C:19]1[CH:18]=[C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[O:16][C:15]=1[C:9]1[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:7]([O:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:8]=1)(=[O:30])[CH3:29]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 24408BromineHCID 10065530HCID 10065530, compound

Product 1

HCID 19361673HCID 19361673, compoundYield 31%

Procedure

A mixture of 2-(3-Cyclopentyloxy-4-methoxyphenyl)-5-(2-pyridyl)furan, (50 mg) from example 2, in acetic acid (2 ml) and bromine were stirred for 15 mins. at room temperature. The reaction mixture was quenched with sodium sulfite extracted with EtOAc dried with sodium sulfate and evaporated in vacuo to afford the unexpected title compound as a beige solid in 31% yield. 1H NMR (300 MHz, CDCl3): δ 1.6 (m, 2H), 1.98-1.8 (m, 6H), 2.3 (s, 3H), 3.88 (s, 3H), 4.82 (m, 1H), 6.91 (dd, 1H), 7.10 (m, 1H), 7.25 (s, 1H), 7.35 (dd, 2H), 7.7 (bs, 2H), 8.58 (d, 1H).

Workup

  1. customat room temperature
  2. customThe reaction mixture was quenched with sodium sulfite
  3. extractionextracted with EtOAc
  4. dry with materialdried with sodium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-6df9dcff540348b8983810d06cdab0d7
Source dataset
uspto-grants-2000_02
Patent number
US06020339

Reaction notes

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