Acetyl chloride → 1-(4-Bromo-2-hydroxynapthalen-1-yl)ethanone

HRID 253227Notes

Reaction equation

HRID 253227 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([OH:12])[CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:17](Cl)(=[O:19])[CH3:18]>ClC(Cl)C>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:17](=[O:19])[CH3:18])=[C:4]([OH:12])[CH:3]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 121155964-Bromo-2-naphthol

Product 1

HCID 668918311-(4-Bromo-2-hydroxynapthalen-1-yl)ethanoneYield 83.4%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 0.625 g (2.80 mmol) 4-bromonapthalen-2-ol in dichloroethane (2.5 mL) was added aluminum chloride (0.561 g, 4.20 mmol), followed by acetyl chloride (0.20 mL, 2.8 mmol). The solution was refluxed for 2 h, then poured into 50 mL ice-cold 1M hydrochloric acid. This solution was extracted with dichloromethane (2×100 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. Column chromatography (SiO2, 3:1 hexanes/ethyl acetate) gave 0.619 g (83%) of 1-(4-bromo-2-hydroxynapthalen-1-yl)ethanone as a pale pink solid. 1H NMR (400 MHz, d6-DMSO): 13.22 (s, 1H), 8.25 (d, 1H), 8.04 (d, 1H), 7.61 (dt, 1H), 7.51 (s, 1H), 7.49 (t, 1H), 2.83 (s, 3H); MS (EI) for C12H9O2Br: 265 (MH+), 267 (M+2).

Workup

  1. temperatureThe solution was refluxed for 2 h
  2. extractionThis solution was extracted with dichloromethane (2×100 mL)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ee2409e12eff49fabdc2befa4810b16c
Source dataset
uspto-grants-2011_01
Patent number
US07872014B2

Reaction notes

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