Boron tribromide → 3-(3-fluoro-4-hydroxyphenyl)-3,4-dihydroquinazolin-2(1H)-one

HRID 2241227Notes

Reaction equation

HRID 2241227 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:10]2[CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][C:11]2=[O:20])[CH:5]=[CH:6][C:7]=1[O:8]C.B(Br)(Br)Br>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([N:10]2[CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][C:11]2=[O:20])[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 685164283-(3-fluoro-4-methoxyphenyl)-3,4-dihydroquinazolin-2(1H)-one

Product 1

HCID 685123673-(3-fluoro-4-hydroxyphenyl)-3,4-dihydroquinazolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-(3-fluoro-4-methoxyphenyl)-3,4-dihydroquinazolin-2(1H)-one (60 mg, 0.22 mmol) in 2.2 mL dichloromethane at 0° C. under a drying tube was added boron tribromide (104 μL, 1.1 mmol) neat by syringe. After 5 minutes, TLC in 1/1 EtOAc/hexanes showed complete consumption of starting material and a new slightly lower rf spot. The reaction was quenched by pouring into saturated NaHCO3 (30 mL) with stirring. 9/1 Dichloromethane/methanol (30 mL) was added and the mixture stirred rapidly. The layers were separated and the organics were dried (MgSO4), filtered, and concentrated to a white solid (40 mg, 70%). LRMS (APCI pos) m/e 259 (M+1). 1H NMR (400 MHz, CDCl3) δ 7.40 (m, 1H), 7.22 (m, 1H), 7.07 (m, 2H), 6.98 (m, 2H), 6.83 (m, 1H), 4.78 (s, 2H).

Workup

  1. customTLC in 1/1 EtOAc/hexanes showed complete consumption of starting material
  2. customThe reaction was quenched
  3. additionby pouring into saturated NaHCO3 (30 mL)
  4. addition9/1 Dichloromethane/methanol (30 mL) was added
  5. stirringthe mixture stirred rapidly
  6. customThe layers were separated
  7. dry with materialthe organics were dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated to a white solid (40 mg, 70%)

Sources & evidence

ORD record
ord-c39dd982fe4c4b76acfb7627ed3ac9df
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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