Bromine → HCID 24831456, compound

HRID 2191082Notes

Reaction equation

HRID 2191082 reaction equation
[N:1]1([C:7]2[S:8][C:9]3[C:15](=[O:16])[CH2:14][CH2:13][CH2:12][C:10]=3[CH:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Br:17]Br>C1COCC1.[Cl-].[Na+].O>[Br:17][C:11]1[C:10]2[CH2:12][CH2:13][CH2:14][C:15](=[O:16])[C:9]=2[S:8][C:7]=1[N:1]1[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 24408BromineHCID 24831302HCID 24831302, compound

Product 1

HCID 24831456HCID 24831456, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirred solution of Example 2 (0.83 g, 3.50 mmol) in THF (50 mL) at 0° C. was added, dropwise, Br2 (0.56 g, 3.50 mmol) and the reaction mixture was stirred for 20 minutes. The reaction mixture was then poured into brine (200 mL) and extracted with EtOAc (3×100 mL). The combined organics were dried over MgSO4, filtered and concentrated in vacuo. Purification by column chromatography (SiO2, 1:5 EtOAc/hexanes) gave the title compound as a pale brown solid (0.79 g, 72%). δH (DMSO-d6) 3.77-3.74 (4H, m), 3.22-3.18 (4H, m), 2.70-2.67 (2H, m), 2.52-2.47 (2H, m), 2.10-2.04 (2H, m). δ 13C (DMSO-d6) 189.7, 160.2, 152.7, 124.6, 97.4, 65.9 (2×CH2), 51.9 (2×CH2), 37.3, 25.9, 23.4. LCMS (ES+) 315.0 and 317.0 (M+H)+.

Workup

  1. extractionextracted with EtOAc (3×100 mL)
  2. dry with materialThe combined organics were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by column chromatography (SiO2, 1:5 EtOAc/hexanes)

Sources & evidence

ORD record
ord-c9a0560318bd4bfba60f617ca25bddc2
Source dataset
uspto-grants-2012_12
Patent number
US08324204B2

Reaction notes

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