Methanol → 5-Amino-2-fluorophenol

HRID 871245Notes

Reaction equation

HRID 871245 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[O:9]C.B(Br)(Br)Br.CO>C(Cl)Cl>[NH2:6][C:5]1[CH:7]=[CH:8][C:2]([F:1])=[C:3]([OH:9])[CH:4]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 27745334-Fluoro-3-methoxyaniline

Product 1

HCID 226414135-Amino-2-fluorophenolYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 4-fluoro-3-methoxyaniline (2.0 g, 14.2 mmol) in CH2Cl2 (20 mL) at 0° C. was added 1.0 M solution of BBr3 in CH2Cl2 (40 mL). It was stirred overnight, at which time the temperature was raised to room temperature. To it was added MeOH and the solvents were removed under reduced pressure. To the residue was added water, basified with saturated NaHCO3, and extracted with EtOAc. Extracts were washed with brine, dried over MgSO4, and concentrated under reduced pressure to afford 5-amino-2-fluorophenol as solid (1.3 g, 73%). 1H NMR (300 MHz, DMSO-d6) δ 9.26 (s, 1H), 6.81 (dd, 1H), 6.34 (dd, 1H), 6.04 (dd, 1H), 4.63 (br, 2H).

Workup

  1. customthe solvents were removed under reduced pressure
  2. additionTo the residue was added water
  3. extractionextracted with EtOAc
  4. washExtracts were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4a7758928d31407da3cf3e39ad72aa3c
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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