2-Bromonaphthalene → 4-(Naphthalen-2-yl)phenol

HRID 884719Notes

Reaction equation

HRID 884719 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[OH:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C1(C)C=CC=CC=1>[CH:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[CH:11][C:2]=1[C:16]1[CH:17]=[CH:18][C:13]([OH:12])=[CH:14][CH:15]=1

Participants

8

Reactant 4

HCID 113722-BromonaphthaleneHCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 27343604-Hydroxyphenylboronic acid

Product 1

HCID 2368684-(Naphthalen-2-yl)phenolYield 2.5%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 2-bromonaphthalene (4.0 g, 19.32 mmol), 4-hydroxyphenylboronic acid (2.9 g, 21.24 mmol), potassium phosphate (14.35 g, 67.61 mmol), tricyclohexyl phosphine (542 mg, 1.93 mmol), toluene (80 mL) and water (4 mL) was added palladium acetate (217 mg, 0.965 mmol) under N2. The reaction mixture was heated to 100° C. for 24 h and then cooled to rt. Water was added and the mixture was extracted with EtOAc. The organic layer was separated, washed with water, brine, dried and concentrated to give crude product. Purification by column chromatography using 10% EtOAc in hexane afforded 105 mg of 4-naphthalen-2-yl-phenol. MS (ES) m/z: 220.07 (M) and 219.04 (M−1).

Workup

  1. temperaturecooled to rt
  2. extractionthe mixture was extracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed with water, brine
  5. customdried
  6. concentrationconcentrated
  7. customto give crude product
  8. customPurification by column chromatography

Sources & evidence

ORD record
ord-311807c4357149e9af4c762267da50a1
Source dataset
uspto-grants-2012_08
Patent number
US08242130B2

Reaction notes

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