Water → 2-(3,4-Dihydroxyphenyl)acetonitrile

HRID 1505098Notes

Reaction equation

HRID 1505098 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C:11]#[N:12])=[CH:9][C:4]=2[O:3]C1.B(Br)(Br)Br.O>C(Cl)Cl>[OH:3][C:4]1[CH:9]=[C:8]([CH2:10][C:11]#[N:12])[CH:7]=[CH:6][C:5]=1[OH:1]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 781783,4-(Methylenedioxy)phenylacetonitrile

Product 1

HCID 109097272-(3,4-Dihydroxyphenyl)acetonitrileYield 54.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of benzo[1,3]dioxol-5-yl-acetonitrile (0.50 g, 3.1 mmol) in CH2Cl2 (15 mL) was added dropwise BBr3 (0.78 g, 3.1 mmol) at −78° C. under N2. The mixture was slowly warmed to room temperature and stirred overnight. H2O (10 mL) was added to quench the reaction and the CH2Cl2 layer was separated. The aqueous phase was extracted with CH2Cl2 (2×7 mL). The combined organics were washed with brine, dried over Na2SO4 and purified by column chromatography on silica gel (Petroleum Ether/EtOAc 5:1) to give (3,4-dihydroxy-phenyl)-acetonitrile (0.25 g, 54%) as a white solid. 1H NMR (DMSO-d6, 400 MHz) δ 9.07 (s, 1 H), 8.95 (s, 1 H), 6.68-6.70 (m, 2 H), 6.55 (dd, J=8.0, 2.0 Hz, 1 H), 3.32 (s, 2 H).

Workup

  1. customto quench
  2. customthe reaction
  3. customthe CH2Cl2 layer was separated
  4. extractionThe aqueous phase was extracted with CH2Cl2 (2×7 mL)
  5. washThe combined organics were washed with brine
  6. dry with materialdried over Na2SO4
  7. custompurified by column chromatography on silica gel (Petroleum Ether/EtOAc 5:1)

Sources & evidence

ORD record
ord-3e9f308a08f647a4939986911ecde0cd
Source dataset
uspto-grants-2015_12
Patent number
US09216969B2

Reaction notes

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