Dichloromethane → 4-Bromo-2-fluoro-6-hydroxybenzonitrile

HRID 2367542Notes

Reaction equation

HRID 2367542 reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([O:10]CC2C=CC=CC=2)[C:5]([C:6]#[N:7])=[C:4]([F:18])[CH:3]=1.C(Cl)Cl.B(Br)(Br)Br>O>[Br:1][C:2]1[CH:9]=[C:8]([OH:10])[C:5]([C:6]#[N:7])=[C:4]([F:18])[CH:3]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 585047342-(Benzyloxy)-4-bromo-6-fluorobenzonitrile

Product 1

HCID 585046304-Bromo-2-fluoro-6-hydroxybenzonitrileYield 80.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 500-mL RBF was added 4-bromo-2-fluoro-6-[(phenylmethyl)oxy]benzonitrile (5 g, 16.33 mmol) and CH2Cl2 (100 mL). The flask was cooled in an ice-water bath and BBr3 (49.0 mL, 49.0 mmol) (solution in CH2Cl2) was added dropwise via syringe. The red solution was allowed to warm to room temperature over 1 hour. The solution was poured into water (200 mL) and extracted with EtOAc (3×200 mL). The combined organics were concentrated to a yellow residue. The residue was treated with CH2Cl2, and a precipitate formed which was collected to afford the title compound (2.830 g) as a fine yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 7.03 (t, J=1.4 Hz, 1H), 7.29 (dd, J=9.0, 1.6 Hz, 1H), 12.23 (s, 1H).

Workup

  1. temperatureThe flask was cooled in an ice-water bath
  2. extractionextracted with EtOAc (3×200 mL)
  3. concentrationThe combined organics were concentrated to a yellow residue
  4. additionThe residue was treated with CH2Cl2
  5. customa precipitate formed which
  6. customwas collected

Sources & evidence

ORD record
ord-1f2076ec44484a13a583c3c987225f4f
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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