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

HRID 1013279Notes

Reaction equation

HRID 1013279 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-e0f05574288145bdae1c7065ba4392e1
Source dataset
uspto-grants-2011_07
Patent number
US07981888B2

Reaction notes

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