Water → 2-Bromo-6,7-dichloro-1-(4-chlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenol

HRID 2164257Notes

Reaction equation

HRID 2164257 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[C:8]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)=[CH:7][CH2:6][CH2:5]2.[OH2:20].[Br:21]NC(=O)C>CC(C)=O>[Br:21][CH:7]1[CH2:6][CH2:5][C:4]2[C:9](=[CH:10][C:11]([Cl:12])=[C:2]([Cl:1])[CH:3]=2)[C:8]1([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[OH:20]

Participants

5

Reactant 3

HCID 962Water2×HCID 4353N-BromoacetamideHCID 204060666,7-Dichloro-4-(4-chlorophenyl)-1,2-dihydronaphthalene

Product 1

HCID 204060682-Bromo-6,7-dichloro-1-(4-chlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenol

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

6,7-Dichloro-1-(4-chlorophenyl)-3,4-dihydronaphthalene (3.0 g.) was dissolved in acetone (80 ml.), then water (30 ml.) was added, followed by a solution of N-bromoacetamide (3.0 g.) in acetone (40 ml.), and the mixture was stirred for 2 hours. The reaction mixture was then poured into water (150 ml.) and extracted with ether (3×80 ml.), the extracts were combined and dried, and the solvent was evaporated under reduced pressure to leave an oil. This residual oil was chromatographed on silica (Merck's Grade 7734), using 30% by volume of diethyl ether in petroleum ether (b.p. 60°-80° C.) as the eluant, to give the required 2-bromo-6,7-dichloro-1-(4-chlorophenyl)-1,2,3,4-tetrahydro-1-naphthol, m.p. 103°-104.5° C.

Workup

  1. extractionextracted with ether (3×80 ml.)
  2. customdried
  3. customthe solvent was evaporated under reduced pressure
  4. customto leave an oil
  5. customThis residual oil was chromatographed on silica (Merck's Grade 7734)

Sources & evidence

ORD record
ord-a7a29f6fdb59420590ea1bdcbe71b044
Source dataset
uspto-grants-1985_03
Patent number
US04503062

Reaction notes

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