Ammonium Chloride → 2-Iodo-7-methoxy-3-phenyl-4-(4-pivaloyloxyphenyl)-1,2,3,4-tetrahydronaphthalene

HRID 1926575Notes

Reaction equation

HRID 1926575 reaction equation
[B-](F)(F)(F)F.C1C=CN=CC=1.C1C=CN=CC=1.[IH2+:18].[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH:27]([C:37]2[CH:42]=[CH:41][C:40]([O:43][C:44](=[O:49])[C:45]([CH3:48])([CH3:47])[CH3:46])=[CH:39][CH:38]=2)[CH:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:29]=[CH2:30])=[CH:23][CH:22]=1.[Cl-].[NH4+]>C(Cl)Cl>[I:18][CH:29]1[CH:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:27]([C:37]2[CH:38]=[CH:39][C:40]([O:43][C:44](=[O:49])[C:45]([CH3:48])([CH3:47])[CH3:46])=[CH:41][CH:42]=2)[C:24]2[C:23](=[CH:22][C:21]([O:20][CH3:19])=[CH:26][CH:25]=2)[CH2:30]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 10883201Bis(pyridine)iodonium tetrafluoroborateHCID 251119881-(4-Methoxyphenyl)-2-phenyl-1-(4-pivaloyloxyphenyl)-3-butene

Product 1

HCID 251119892-Iodo-7-methoxy-3-phenyl-4-(4-pivaloyloxyphenyl)-1,2,3,4-tetrahydronaphthaleneYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

Bis(pyridine)iodonium tetrafluoroborate (65.8 mg, 0.177 mmol) was suspended in methylene chloride (3.4 mL), and cooled in a dry ice-acetone bath to −78° C. To this, a methylene chloride (1.8 mL) solution of 1-(4-methoxyphenyl)-2-phenyl-1-(4-pivaloyloxyphenyl)-3-butene (4, 56.0 mg, 0.135 mmol) was added, and further, boron tribromide diethyl ether complex (0.015 mL, 0.118 mmol) was added divided into 3 portions. After this, and after stirring for 1 hr at −78° C., the reaction was stopped by adding a saturated ammonium chloride solution (5 mL), and after returning to room temperature, extraction was performed three times with diethyl ether (10 mL). The organic layers were combined and washed with a saturated sodium chloride solution (10 mL), dried with anhydrous sodium sulfate, and concentrated. The residue was purified with thin layer chromatography (toluene), and the subject compound (5, 51.6 mg) was obtained as a slightly yellow oily substance (yield 71%).

Workup

  1. additionfurther, boron tribromide diethyl ether complex (0.015 mL, 0.118 mmol) was added
  2. customafter returning to room temperature
  3. extractionextraction
  4. washwashed with a saturated sodium chloride solution (10 mL)
  5. dry with materialdried with anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified with thin layer chromatography (toluene)
  8. customthe subject compound (5, 51.6 mg) was obtained as a slightly yellow oily substance (yield 71%)

Sources & evidence

ORD record
ord-c40d948747ba4fe3b5d4944586b66968
Source dataset
uspto-grants-2012_05
Patent number
US08183235B2

Reaction notes

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