Bromide ion → 5-Cyclopropyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol

HRID 863549Notes

Reaction equation

HRID 863549 reaction equation
[Br-].[CH:2]1[C:12]2[CH2:11][CH2:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[C:7](=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+].Cl.[CH2:21]1[CH2:25]OC[CH2:22]1>>[CH:22]1([C:7]2([OH:17])[C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[CH2:10][CH2:11][C:12]3[CH:2]=[CH:3][CH:4]=[CH:5][C:6]2=3)[CH2:21][CH2:25]1

Participants

6

Reactant 5

HCID 259Bromide ionHCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 14589DibenzosuberoneHCID 25517Ammonium Chloride

Product 1

HCID 192613825-Cyclopropyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol

Procedure

A solution of cycloprolpylmagnesium bromide in dry THF (prepared from cyclopropylbromide (12.1 g, 0.10 mol), magnesium turnings (2.45 g, 0.10 mol) and dry THF (65 ml)) was placed under an atmosphere of nitrogen. A solution of 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one (10.4 g, 0.05 mol) in dry THF (25 ml) was added dropwise and when addition was complete the mixture was heated at reflux for 30 minutes. The reaction mixture was cooled on an ice-bath and saturated ammonium chloride (50 ml) was carefully added. The mixture was neutralized with 2N hydrochloric acid and extracted with diethyl ether (2×200 ml). The combined organic extracts were dried (Na2SO4) and the solvent was evaporated in vacuo to give 13.1 g of crude 5-cyclopropyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol.

Workup

  1. additionwhen addition
  2. temperaturewas heated
  3. temperatureat reflux for 30 minutes
  4. temperatureThe reaction mixture was cooled on an ice-bath
  5. extractionextracted with diethyl ether (2×200 ml)
  6. dry with materialThe combined organic extracts were dried (Na2SO4)
  7. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-55d1f7aa50f34f48b6590d7aaecd6ff5
Source dataset
uspto-grants-1998_02
Patent number
US05721254

Reaction notes

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