Boron tribromide → Methyl 6-hydroxybenzofuran-3-carboxylate

HRID 1865214Notes

Reaction equation

HRID 1865214 reaction equation
C[O:2][C:3]1[CH:15]=[CH:14][C:6]2[C:7]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][O:9][C:5]=2[CH:4]=1.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:15]=[CH:14][C:6]2[C:7]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][O:9][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 53419774Methyl 6-methoxybenzofuran-3-carboxylate

Product 1

HCID 59577559Methyl 6-hydroxybenzofuran-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methyl 6-methoxybenzofuran-3-carboxylate (498 mg, 2.42 mmol) was dissolved in dichloromethane (100 mL) then cooled to −10 C. A solution of 1M boron tribromide in dichloromethane (9.67 mL, 9.67 mmol) was added slowly via syringe. The dark purple reaction mixture was warmed to RT over 3 h then continued stirring at RT for an additional 4 h. The mixture was slowly quenched with aqueous 1N hydrochloric acid until it became colorless. The mixture was diluted with dichloromethane and washed with water (2×) and brine. The organic layer was dried over sodium sulfate and concentrated in vacuo. The remaining orange-brown solid was purified by silica gel chromatography (1:4 EtOAc/hexane) to afford methyl 6-hydroxybenzofuran-3-carboxylate as an off-white solid. MS (ESI, neg. ion) m/z: 191.1 (M−1).

Workup

  1. temperaturethen cooled to −10 C
  2. customThe mixture was slowly quenched with aqueous 1N hydrochloric acid until it
  3. additionThe mixture was diluted with dichloromethane
  4. washwashed with water (2×) and brine
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe remaining orange-brown solid was purified by silica gel chromatography (1:4 EtOAc/hexane)

Sources & evidence

ORD record
ord-1dec84f93e2044b7a94e52dd0379f587
Source dataset
uspto-grants-2009_12
Patent number
US07626030B2

Reaction notes

Loading…