Bromoform → HCID 19761778, compound

HRID 249465Notes

Reaction equation

HRID 249465 reaction equation
C(Cl)Cl.[CH:4]([Br:7])(Br)[Br:5].[O:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]=[CH2:23])[C:17]=1[CH3:24].[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O.C(O)C>[O:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]2[CH2:23][C:4]2([Br:7])[Br:5])[C:17]=1[CH3:24]

Participants

8

Reactant 4

HCID 5558BromoformHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 19761783HCID 19761783, compound

Product 1

HCID 19761778HCID 19761778, compoundYield 53.6%

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Dihalocarbene addition: 10 ml of methylene chloride, 0.42 ml of ethanol, 0.14 g of benzyltriethyl-ammonium chloride and 20.9 g (0.083 mole) of bromoform are added to 9.9 g (0.042 mole) of 2-methyl-3-vinylbenzyl tetrahydro-2-pyranyl ether. After the addition of 13.28 g (0.166 mole) of ice-cold 50% strength NaOH, thorough stirring is carried out for 1 hour at room temperature and for 8 hours at 50° C. The reaction mixture is poured into 300 ml of water and is extracted three times with methylene chloride. The combined extracts are dried and evaporated down. Purification by column chromatography over silica gel using toluene as the mobile phase gives 9.1 g of 3-(2',2'-dibromocyclopropyl)2-methylbenzyl tetrahydro-2-pyranyl ether.

Workup

  1. extractionis extracted three times with methylene chloride
  2. customThe combined extracts are dried
  3. customevaporated down
  4. customPurification by column chromatography over silica gel

Sources & evidence

ORD record
ord-2bd881c595094f6e9d644491cae09607
Source dataset
uspto-grants-1993_05
Patent number
US05214187

Reaction notes

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