2-Bromoethanol → HCID 18943943, compound

HRID 400100Notes

Reaction equation

HRID 400100 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH2:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[CH:7]([OH:16])[C:6]=2[CH:17]=1.[Br:18][CH2:19][CH2:20]O>C1C=CC=CC=1.S(=O)(=O)(O)O>[Br:18][CH2:19][CH2:20][O:16][CH:7]1[C:6]2[CH:17]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[CH2:11][CH2:10][C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]1=2

Participants

5

Reactant 2

HCID 108982-BromoethanolHCID 18943942HCID 18943942, compound

Product 1

HCID 18943943HCID 18943943, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 3-chloro-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol (3.52 g, 0.014 mol, prepared similarly as described in Fr.M. 2165, 1963; Chem.Abstr. 60, 14523 (1963)) and 2bromoethanol (2.5 g, 0.02 mol) in benzene (80 ml), concentrated sulfuric acid (0.85 ml) was added dropwise. The reaction mixture was stirred for 1.5 h, diluted with 50 ml of benzene and washed with water (30 ml), 0.6 N NaHCO3 (20 ml) and 2×30 ml of water. The benzene solution was dried (MgSO4) and the solvent was evaporated under vacuum to give a residue which was crystallised from a mixture of cyclohexane and n-hexane. 3.9 g (77%) of 5-(2-bromoethoxy)-3-chloro-10,11-dihydro-5H-dibenzo[a,d]cycloheptene was obtained.

Workup

  1. washwashed with water (30 ml), 0.6 N NaHCO3 (20 ml) and 2×30 ml of water
  2. dry with materialThe benzene solution was dried (MgSO4)
  3. customthe solvent was evaporated under vacuum
  4. customto give a residue which
  5. customwas crystallised from a mixture of cyclohexane and n-hexane

Sources & evidence

ORD record
ord-0d46376dd12d4fdfbf9cf0a6692cfb99
Source dataset
uspto-grants-1998_10
Patent number
US05827856

Reaction notes

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