Boron Trichloride → HCID 67352443, compound

HRID 2272285Notes

Reaction equation

HRID 2272285 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[C:18]([O:24]C(C)C)=[CH:17][C:11]=3[C:12]=2[C:13]([O:15][CH3:16])=[O:14])=[CH:4][CH:3]=1.B(Cl)(Cl)Cl>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]3[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[C:18]([OH:24])=[CH:17][C:11]=3[C:12]=2[C:13]([O:15][CH3:16])=[O:14])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 67355472HCID 67355472, compound

Product 1

HCID 67352443HCID 67352443, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of methyl 2-(4-fluorophenyl)-5-[(1-methylethyl)oxy]-6-nitro-1-benzofuran-3-carboxylate (5.237 g, 14.03 mmol) in dry dichloromethane (70 mL) at −15° C., under an atmosphere of nitrogen, was added a 1M solution of boron trichloride in dichloromethane (23.85 mL, 23.85 mmol) over 30 minutes using a syringe pump. The dark brown-red reaction mixture was poured over ice (˜250 mL). The ice was allowed to melt and the mixture extracted with dichloromethane (˜450 mL). The organic phase was separated by hydrophobic filter tube and evaporated under vacuum to give the methyl 2-(4-fluorophenyl)-5-hydroxy-6-nitro-1-benzofuran-3-carboxylate. 1H NMR (d6-DMSO): δ 10.97 (1H, br. s), 8.34 (1H, s), 8.07 (2H, dd), 7.67 (1H, s), 7.43 (2H, t), 3.86 (3H, s).

Workup

  1. extractionthe mixture extracted with dichloromethane (˜450 mL)
  2. customThe organic phase was separated by hydrophobic filter tube
  3. customevaporated under vacuum

Sources & evidence

ORD record
ord-2a36436c667343a1992383386979c14e
Source dataset
uspto-grants-2015_09
Patent number
US09119868B2

Reaction notes

Loading…