Dichloromethane → HCID 59560835, compound

HRID 1176971Notes

Reaction equation

HRID 1176971 reaction equation
[CH2:1]([O:13][C:14]1[CH:15]=[C:16]([C:33]2([CH:39]([C:41]3[CH:46]=[CH:45][C:44]([I:47])=[CH:43][CH:42]=3)[OH:40])SCCCS2)[CH:17]=[CH:18][C:19]=1[O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C1C(=O)N(Br)C(=[O:51])C1.[O-]S([O-])=O.[Na+].[Na+].C(Cl)Cl>CC(C)=O.O.CC(C)=O>[CH2:1]([O:13][C:14]1[CH:15]=[C:16]([C:33](=[O:51])[C:39]([C:41]2[CH:46]=[CH:45][C:44]([I:47])=[CH:43][CH:42]=2)=[O:40])[CH:17]=[CH:18][C:19]=1[O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 24437Sodium SulfiteHCID 67184N-bromobutanimideHCID 72326541HCID 72326541, compound

Product 1

HCID 59560835HCID 59560835, compoundYield 25.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 18366337Propan-2-one--water (1/1)Solvent

Conditions

Temperature
12.5 °C

Procedure

A solution of [2-(3,4-bis-dodecyloxy-phenyl)-[1,3]dithian-2-yl]-(4-iodo-phenyl)-methanol (JYC-II-020-A) (8.2 g, 10.3 mmol) in 400 mL of acetone was added dropwise to a solution of NBS (31.86 g, 17.9 mmol) in 3% water/acetone (v/v) at 0° C. The reaction mixture was stirred at 0-25° C. for 30 min. It was then poured into a saturated aqueous Na2SO3 solution (400 mL) and CH2Cl2 (400 mL) mixture. The resulting mixture was stirred at room temperature for additional 10 min. The organic layer was washed with H2O and dried over anhydrous MgSO4. The solvent was removed under reduced pressure. The crude product was recrystallized from hexanes. The product was further purified by column chromatography (silica gel, hexanes:dichloromethane=2:1 (v/v)) to give a light yellow solid (1.84 g, 25.4%). 1H NMR (300 MHz, CDCl3, δ): 7.85 (d, J=8.5 Hz, 2H), 7.65 (d, J=8.5 Hz, 2H), 7.53 (d, J=1.9 Hz, 1H), 7.38 (dd, J=8.5 Hz, 1.9 Hz, 1H), 6.83 (d, J=8.2 Hz, 1H), 4.04 (t, J=6.6 Hz, 2H), 4.03 (t, J=6.6 Hz, 2H), 1.76-1.86 (m, 4H), 1.20-1.51 (m, 36H), 0.86 (t, J=6.3 Hz, 6H). 13C {1H} NMR (75 MHz, CDCl3, δ): 193.77, 192.45, 155.19, 149.28, 138.17, 132.46, 130.90, 126.16, 125.47, 111.94, 111.46, 103.28, 69.21, 69.15, 32.00, 29.75, 29.70, 29.66, 29.45, 29.40, 29.10, 28.94, 26.06, 25.98, 22.78, 14.24. HRMS-EI (m/z): [M]+ calcd for C38H57IO4, 704.33016; found, 704.32941. Anal. calcd for C38H57IO4: C, 64.76; H, 8.15. Found: C, 64.81; H, 8.15.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for additional 10 min
  2. washThe organic layer was washed with H2O
  3. dry with materialdried over anhydrous MgSO4
  4. customThe solvent was removed under reduced pressure
  5. customThe crude product was recrystallized from hexanes
  6. customThe product was further purified by column chromatography (silica gel, hexanes:dichloromethane=2:1 (v/v))

Sources & evidence

ORD record
ord-534cbc56053b4a86a512b8b865a4eff3
Source dataset
uspto-grants-2010_11
Patent number
US07842830B2

Reaction notes

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