Water → 4-(5-Phenyl-2-thienyl)-2-naphthol

HRID 2369639Notes

Reaction equation

HRID 2369639 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]([C:17]2[S:18][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:20][CH:21]=2)[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2.O>ClCCl>[C:22]1([C:19]2[S:18][C:17]([C:9]3[C:10]4[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=4)[CH:16]=[C:7]([OH:6])[CH:8]=3)=[CH:21][CH:20]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 582741703-Methoxy-1-(5-phenyl-2-thienyl)naphthalene

Product 1

HCID 582741834-(5-Phenyl-2-thienyl)-2-naphtholYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (1.04 ml, 10.76 mmol) was added slowly to a solution of 3-methoxy-1-(5-phenyl-2-thienyl)naphthalene (1.7 g, 5.38 mmol) in dichloromethane (50 ml) at 0° C. under nitrogen. After the addition was complete, the solution was allowed to stir for 20 h. The mixture was then poured into water (200 ml), extracted with Et2O (2×100 ml), washed with water (100 ml), dried (Na2SO4) and the solvent removed under reduced pressure. The resulting solid was washed with hexane and filtered to afford the title compound (1.47 g, 91%) as a red solid.

Workup

  1. additionAfter the addition
  2. extractionextracted with Et2O (2×100 ml)
  3. washwashed with water (100 ml)
  4. dry with materialdried (Na2SO4)
  5. customthe solvent removed under reduced pressure
  6. washThe resulting solid was washed with hexane
  7. filtrationfiltered

Sources & evidence

ORD record
ord-f6c360f0862e43a19b9c6153e3cebf90
Source dataset
uspto-grants-2014_04
Patent number
US08703978B2

Reaction notes

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