Boron tribromide → HCID 59152646, compound

HRID 1804788Notes

Reaction equation

HRID 1804788 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]2[CH:11]=[CH:12][C:13]([O:15]C)=[CH:14][C:9]=2[O:8][CH:7]=1)=[O:5])[CH3:2].B(Br)(Br)Br.C(=O)([O-])O.[Na+]>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[C:10]2[CH:11]=[CH:12][C:13]([OH:15])=[CH:14][C:9]=2[O:8][CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 45489697Ethyl 6-methoxybenzofuran-3-carboxylate

Product 1

HCID 59152646HCID 59152646, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

6-Methoxy-benzofuran-3-carboxylic acid ethyl ester (25) (9.3 g, 42 mmol) is dissolved in 80 ml of dichloromethane and cooled to 0° C. 1M solution of BBr3 in dichloromethane (84.5 ml, 84.5 mmol) is added and the mixture is stirred at rt for 2 h. The mixture is poured on ice water and neutralized with sodium hydrogen carbonate. The organic layer is dried over sodium D sulfate, filtrated and evaporated under reduced pressure.

Workup

  1. dry with materialThe organic layer is dried over sodium D sulfate
  2. filtrationfiltrated
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f678b354a0c2452d81b94675c068789d
Source dataset
uspto-grants-2013_01
Patent number
US08354431B2

Reaction notes

Loading…