1,5-Dibromopentane → HCID 57995642, compound

HRID 385387Notes

Reaction equation

HRID 385387 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:5]=[C:6]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[C:7]=1[O:8][CH2:9][C:10]([F:13])([F:12])[F:11].[H-].[Na+].Br[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]Br.[NH4+].[Cl-]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:24]2([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)[CH:5]=[C:6]([C:14]2[CH:15]=[CH:16][C:17]([C:20]([F:21])([F:22])[F:23])=[CH:18][CH:19]=2)[C:7]=1[O:8][CH2:9][C:10]([F:13])([F:12])[F:11]

Participants

6

Reactant 4

HCID 81001,5-DibromopentaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 57995666HCID 57995666, compound

Product 1

HCID 57995642HCID 57995642, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 2-(5-chloro-6-(2,2,2-trifluoroethoxy)-4′-(trifluoromethyl)biphenyl-3-yl)acetate (0.5 g, 1.13 mmol) was dissolved in anhydrous DMF (30 mL), NaH (60% wt. in paraffin oil, 0.113 g, 2.8 mmol) was added at 0° C. The reaction mixture was stirred for 30 min at room temperature and 1,5-dibromopentane (0.19 g, 1.24 mmol) was added drop wise at 0° C. The reaction mixture was stirred an additional 1 h at 0° C. and saturated NH4Cl solution (10 mL) was added. The reaction mixture was extracted with EtOAc (3×20 mL) and the combined organic phases were washed with water (3×20 mL) and brine (20 mL), and dried over MgSO4. The volatiles were removed under reduced pressure and the residue was purified by flash column chromatography to yield compound ethyl 1-(5-chloro-6-(2,2,2-trifluoroethoxy)-4′-(trifluoromethyl)biphenyl-3-yl)-cyclohexanecarboxylate (0.37 g) as a thick liquid.

Workup

  1. stirringThe reaction mixture was stirred an additional 1 h at 0° C.
  2. extractionThe reaction mixture was extracted with EtOAc (3×20 mL)
  3. washthe combined organic phases were washed with water (3×20 mL) and brine (20 mL)
  4. dry with materialdried over MgSO4
  5. customThe volatiles were removed under reduced pressure
  6. customthe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-f1d2e644e9274ef0b677427c02bb719b
Source dataset
uspto-grants-2013_02
Patent number
US08367863B2

Reaction notes

Loading…