Ammonium Chloride → [trans-2-Bromo-4-(2,4-dichlorophenyl)-5-nitrocyclohex-1-en-1-yl]methanol

HRID 1172325Notes

Reaction equation

HRID 1172325 reaction equation
C(O)C.CC(O)C.[Br:8][C:9]1[CH2:14][C@@H:13]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])[C@H:12]([N+:23]([O-:25])=[O:24])[CH2:11][C:10]=1[CH:26]=[O:27].[BH4-].[Na+].[NH4+].[Cl-]>C(OCC)(=O)C>[Br:8][C:9]1[CH2:14][C@@H:13]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])[C@H:12]([N+:23]([O-:25])=[O:24])[CH2:11][C:10]=1[CH2:26][OH:27]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 22179027Isopropanol ethanolHCID 87567943trans-2-Bromo-4-(2,4-dichlorophenyl)-5-nitrocyclohex-1-ene-1-carbaldehyde

Product 1

HCID 68772372[trans-2-Bromo-4-(2,4-dichlorophenyl)-5-nitrocyclohex-1-en-1-yl]methanolYield 84.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a cold (0° C.) ethanol/2-propanol (3 mL/3 mL) solution of Example 7B (758 mg, 2 mmol) under N2 flow, NaBH4 (80 mg, 2.1 mmol) was added. The reaction mixture was stirred and the temperature was allowed to increase from 0° C. to room temperature over two hours. The solution was treated with saturated NH4Cl, and diluted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate, and then filtered. The filtrate was concentrated under reduced pressure and then purified by flash chromatography with 30% ethyl acetate/hexane to provide the title compound (642 mg, 84%). 1H NMR (300 MHz, CDCl3) δ ppm 7.39-7.51 (m, 1H), 7.26-7.32 (m, 1H), 7.11-7.22 (m, 1H), 5.04-5.20 (m, 1H), 4.31-4.45 (m, 2H), 4.14-4.27 (m, 1H), 2.59-3.32 (m, 4H). MS (DCI) m/z 399 (M+H)+.

Workup

  1. temperatureto increase from 0° C. to room temperature over two hours
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. custompurified by flash chromatography with 30% ethyl acetate/hexane

Sources & evidence

ORD record
ord-91c97d499408451fb9bca2c7dc93442b
Source dataset
uspto-grants-2010_11
Patent number
US07834012B2

Reaction notes

Loading…