Bromoform → HCID 69250964, compound

HRID 902759Notes

Reaction equation

HRID 902759 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:8]=1)=[CH2:6])[CH3:2].[CH:22]([Br:25])(Br)[Br:23].[OH-].[Na+]>C(Cl)Cl.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:5]1([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:8]=2)[CH2:6][C:22]1([Br:25])[Br:23])=[O:21])[CH3:2]

Participants

6

Reactant 3

HCID 5558BromoformHCID 14798Sodium HydroxideHCID 69253409HCID 69253409, compound

Product 1

HCID 69250964HCID 69250964, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

Intermediates d-e were prepared following the procedure of Kirmse, W.; Rode, J. Chem. Ber. 1986, 119, 3694-3703. To absolution of 2-(3-benzyloxy-phenyl)-acrylic acid ethyl ester (250 mg, 0.89 mmol) in methylene chloride (283 uL) was added bromoform (100 uL, 1.1 mmol), benzyltriethyl ammonium chloride (2.6 mg), and sodium hydroxide (50% aqueous solution, 167 uL). The reaction was stirred at room temperature for 48 hours and then the product was extracted into diethyl ether, dried (MgSO4), and evaporated. This material was further purified by filtration through a plug of silica gel using diethyl ether as the eluant to give 358 mg (89% yield) of the title compounds as a white solid. MS (ESI) 454.8 (M+H+).

Workup

  1. customIntermediates d-e were prepared
  2. extractionthe product was extracted into diethyl ether
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. filtrationThis material was further purified by filtration through a plug of silica gel

Sources & evidence

ORD record
ord-85dce64279994ce5936ec36bf05aba6d
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

Loading…