Cyclohexane, (bromomethyl)- → HCID 10921586, compound

HRID 401218Notes

Reaction equation

HRID 401218 reaction equation
Br[CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.CON(C)[C:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1COCC1>[CH:3]1([CH2:2][C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:19])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 137636Cyclohexane, (bromomethyl)-HCID 569575N-Methoxy-N-methylbenzamide

Product 1

HCID 10921586HCID 10921586, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of Mg (735 mg, 30.5 mmol) in anhydrous THF (20 mL) was added (bromomethyl)cyclohexane (5.4 g, 30.5 mmol) at 10° C. under N2 atmosphere. The resulting mixture was stirred at reflux until all of Mg was consumed. Then the resulting mixture was cooled to ambient temperature and N-methoxy-N-methylbenzamide (1.0 g, 6.1 mmol) was added and the mixture was stirred at 10° C. for 2 hours. The mixture was quenched with aqueous saturated NH4Cl (50 mL). Followed a standard aqueous/EtOAc workup and the residue was purified by column chromatography on silica gel (PE:EtOAc=20:1) to give Intermediate 96 as colorless oil (800 mg, yield 67%).

Workup

  1. temperatureat reflux until all of Mg
  2. customwas consumed
  3. stirringthe mixture was stirred at 10° C. for 2 hours
  4. customThe mixture was quenched with aqueous saturated NH4Cl (50 mL)
  5. customFollowed a standard aqueous/EtOAc workup and the residue was purified by column chromatography on silica gel (PE:EtOAc=20:1)

Sources & evidence

ORD record
ord-e2512107ff474aefb7dd7f5ba29ce8db
Source dataset
uspto-grants-2014_06
Patent number
US08741915B2

Reaction notes

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