1-bromo-3-ethoxypropane → 5-(3-Ethoxypropyl)-3-iodo-5H-dibenzo[a,d]cyclohepten-5-ol

HRID 225050Notes

Reaction equation

HRID 225050 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][CH2:6]Br)[CH3:2].[I:8][C:9]1[CH:10]=[CH:11][C:12]2[CH:18]=[CH:17][C:16]3[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=3[C:14](=[O:23])[C:13]=2[CH:24]=1>C1COCC1>[CH2:1]([O:3][CH2:4][CH2:5][CH2:6][C:14]1([OH:23])[C:13]2[CH:24]=[C:9]([I:8])[CH:10]=[CH:11][C:12]=2[CH:18]=[CH:17][C:16]2[CH:19]=[CH:20][CH:21]=[CH:22][C:15]1=2)[CH3:2]

Participants

4

Reactant 2

HCID 2604931-bromo-3-ethoxypropaneHCID 202322053-iodo-5H-dibenzo[a,d]cyclohepten-5-one

Product 1

HCID 233288705-(3-Ethoxypropyl)-3-iodo-5H-dibenzo[a,d]cyclohepten-5-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Ethoxypropyl bromide (7.5 g., 0.045 mole) is converted to the Grignard reagent using standard procedures (see above). To this solution (ca 60 ml.), stirred in an ice bath, is added dropwise a solution of 10 g. (0.030 mole) of 3-iodo-5H-dibenzo[a,d]cyclohepten-5-one in 30 ml. of dry THF. The mixture is stirred for 5 minutes and concentrated in vacuo. The residue is treated with saturated ammonium chloride solution and extracted three times with ether. The ether layer is washed once with water, dried over sodium sulfate, and evaporated in vacuo to an orange solid, m.p. 95°-105° (12.0 g., 95%).

Workup

  1. additionis added dropwise a solution of 10 g
  2. stirringThe mixture is stirred for 5 minutes
  3. concentrationconcentrated in vacuo
  4. additionThe residue is treated with saturated ammonium chloride solution
  5. extractionextracted three times with ether
  6. washThe ether layer is washed once with water
  7. dry with materialdried over sodium sulfate
  8. customevaporated in vacuo to an orange solid, m.p. 95°-105° (12.0 g., 95%)

Sources & evidence

ORD record
ord-6e426573da884e4b95107a3bac12fab8
Source dataset
uspto-grants-1980_11
Patent number
US04235820

Reaction notes

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