Ethanol → HCID 19079050, compound

HRID 963974Notes

Reaction equation

HRID 963974 reaction equation
[CH:1]1[C:11]2[C:10](=[CH:12][CH2:13][OH:14])[C:9]3[CH:15]=[CH:16][CH:17]=[CH:18][C:8]=3[CH2:7][O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH2:19]([OH:21])[CH3:20].[Br:22]N1C(=O)CCC1=O.C([O-])(O)=O.[Na+]>ClCCl>[Br:22][CH:12]([C:10]1([O:21][CH2:19][CH3:20])[C:9]2[CH:15]=[CH:16][CH:17]=[CH:18][C:8]=2[CH2:7][O:6][C:5]2[CH:4]=[CH:3][CH:2]=[CH:1][C:11]1=2)[CH2:13][OH:14]

Participants

6

Reactant 4

HCID 702EthanolHCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 54450619HCID 54450619, compound

Product 1

HCID 19079050HCID 19079050, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolved 2-[6,11-dihydro-dibenz[b,e]oxepin-11-ylidene]-ethanol (10.90 g, 0.0457 mol) in 175 mL of dichloromethane. Added ethanol (21.07 g, 26.8 mL, 0.457 mol), and cooled to 0° C. under a nitrogen atmosphere. Added N-bromosuccinimide (8.96 g, 0.0503 mol) portionwise. Warmed slowly to room temperature over 60 mins. Added 200 mL of saturated NaHCO3, and separated layers. Extracted aqueous solution with dichloromethane. Dried combined organic extracts with MgSO4, filtered, and evaporated. Purified crude product by flash chromatography on silica gel eluting with 1:4 ethyl acetate:hexane. Combined appropriate fractions, and evaporated to give 14.35 g (86% yield) of 2-bromo-2-[6,11-dihydro-11-ethoxy-dibenz[b,e]oxepin-11-yl]-ethanol as a light yellow oil. ##STR43##

Workup

  1. customseparated layers
  2. customDried
  3. filtrationfiltered
  4. customevaporated
  5. customPurified crude product by flash chromatography on silica gel eluting with 1:4 ethyl acetate
  6. customevaporated

Sources & evidence

ORD record
ord-f6046d4a0e7f4fdc955c92042f504938
Source dataset
uspto-grants-1998_06
Patent number
US05767120

Reaction notes

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