1-Naphthol → 1-(3-Bromopropoxy)naphthalene

HRID 533239Notes

Reaction equation

HRID 533239 reaction equation
[C:1]1([OH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Br:12][CH2:13][CH2:14][CH2:15]O.C(OC(N=NC(OC(C)(C)C)=O)=O)(C)(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Br:12][CH2:13][CH2:14][CH2:15][O:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 70051-NaphtholHCID 11776TriphenylphosphineHCID 123083-Bromo-1-propanolHCID 97268Di-tert-butyl azodicarboxylate

Product 1

HCID 129593811-(3-Bromopropoxy)naphthalene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-naphthol (3.45 g), 3-bromopropanol (1.75 mL), di-t-butyl-azo-dicarboxylate (5.52 g) and triphenylphosphine (6.28 g) in THF (30 mL) was stirred at room temperature for 16 hours and concentrated. The concentrate was diluted with ethyl acetate, washed with water and brine and dried (MgSO4), filtered, and concentrated. The concentrate was purified by silica gel chromatography with 0-7% ethyl acetate/hexane.

Workup

  1. concentrationconcentrated
  2. additionThe concentrate was diluted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by silica gel chromatography with 0-7% ethyl acetate/hexane

Sources & evidence

ORD record
ord-72a5658948084de9a608723cb25eafd4
Source dataset
uspto-grants-2014_10
Patent number
US08853209B2

Reaction notes

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