2-(Benzyloxy)-5-fluorobenzonitrile → 5-Fluoro-2-hydroxybenzonitrile

HRID 1665987Notes

Reaction equation

HRID 1665987 reaction equation
C([O:8][C:9]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:10]=1[C:11]#[N:12])C1C=CC=CC=1>CO>[F:17][C:14]1[CH:15]=[CH:16][C:9]([OH:8])=[C:10]([CH:13]=1)[C:11]#[N:12]

Participants

3

Reactant 1

HCID 582814722-(Benzyloxy)-5-fluorobenzonitrile

Product 1

HCID 129192915-Fluoro-2-hydroxybenzonitrileYield 106%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dry 10% Pd/C (2.48 g) was placed in a 5 L flask under N2. A solution of 2-(benzyloxy)-5-fluorobenzonitrile (148 g, 651 mmol) in methanol (2.34 L) was added slowly under N2. The air of the flask was removed by vacuum and the flask was charged with H2 (balloon) three times. The mixture was stirred at room temperature for 1 hour. The above process was repeated two more times to push the reaction to completion. The mixture was stirred at room temperature for another 2 hours. The mixture was filtered through a Celite pad under N2 and washed with EtOAc (150 mL×2). The palladium waste was rinsed with water (50 mL) and discarded. The filtrates were concentrated to give (94.6 g, 106%) of the desired compound as a yellow solid. MS (APCI-) m/z 137 (M−1) was detected. 1H NMR (400 MHz, DMSO-d6) δ 11.07 (br, 1H), 7.58 (dd, 1H, J=3.2 Hz, J=8.2 Hz), 7.43 (m, 1H), 6.91-7.03 (dd, 1H J=4.5 Hz, J=9.2 Hz).

Workup

  1. dry with materialDry 10% Pd/C (2.48 g)
  2. customwas placed in a 5 L flask under N2
  3. customThe air of the flask was removed by vacuum
  4. additionthe flask was charged with H2 (balloon) three times
  5. customthe reaction to completion
  6. stirringThe mixture was stirred at room temperature for another 2 hours
  7. filtrationThe mixture was filtered through a Celite pad under N2
  8. washwashed with EtOAc (150 mL×2)
  9. washThe palladium waste was rinsed with water (50 mL)
  10. concentrationThe filtrates were concentrated

Sources & evidence

ORD record
ord-96dfe1f4fe8a4a929a7ec55259b595c2
Source dataset
uspto-grants-2011_10
Patent number
US08039639B2

Reaction notes

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