Allyl bromide → HCID 58361498, compound

HRID 2076452Notes

Reaction equation

HRID 2076452 reaction equation
[C:1]1([S:7]([O:10][C:11]2[C:20]([Br:21])=[C:19]3[C:14]([CH:15]=[CH:16][C:17]([CH:22]=[O:23])=[N:18]3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:24](Br)[CH:25]=[CH2:26]>C1COCC1.[NH4+].[Cl-]>[C:1]1([S:7]([O:10][C:11]2[C:20]([Br:21])=[C:19]3[C:14]([CH:15]=[CH:16][C:17]([CH:22]([OH:23])[CH2:26][CH:25]=[CH2:24])=[N:18]3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 7841Allyl bromideHCID 58361485HCID 58361485, compound

Product 1

HCID 58361498HCID 58361498, compoundYield 96.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

A mixture of compound 16 (448 mg, 1.14 mmol), In powder (150 mg, 1.31 mmol) and allyl bromide (160 μL, 1.87 mmol) were stirred in a mixture of 10 mL THF and 10 mL aq. NH4Cl for 3 hours. THF was removed in vacuo, and residue was extracted with EtOAc and then dried over anhydrous Na2SO4. Solvent was removed in vacuo, and the residue was purified by SiO2 column chromatography (hexanes/EtOAc=2/1) to yield 17 as a colorless oil (478 mg, 1.10 mmol, 96% yield). 1H NMR (500 MHz, CDCl3) δ 8.13 (d, 1H, J=8.0 Hz), 7.96−7.93 (m, 2H), 7.76 (d, 1H, J=9.0 Hz), 7.68 (t, 1H, J=8.5 Hz), 7.54−7.50 (m, 3H), 7.42 (d, 1H, J=8.5 Hz), 5.89−5.80 (m, 1H), 5.11−5.03 (m, 2H), 4.97 (s, 2H), 2.73−2.69 (m, 1H), 2.54−2.48 (m, 1H). 13C NMR (500 MHz, CDCl3) δ 163.40, 148.17, 144.08, 137.34, 135.61, 134.86, 133.88, 129.40, 128.67, 128.01, 126.84, 122.47, 119.53, 118.22, 118.12, 72.24, 42.34. MS-ESI (m/z): [M+H]+ calculated for C19H17BrNO4S, 434.01 (79Br) and 436.00 (81Br); found 434.11 (79Br) and 436.10 (81Br).

Workup

  1. customTHF was removed in vacuo, and residue
  2. extractionwas extracted with EtOAc
  3. dry with materialdried over anhydrous Na2SO4
  4. customSolvent was removed in vacuo
  5. customthe residue was purified by SiO2 column chromatography (hexanes/EtOAc=2/1)

Sources & evidence

ORD record
ord-c2a02a5e458944c68d7946af9a7bf529
Source dataset
uspto-grants-2011_04
Patent number
US07923562B2

Reaction notes

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