Water → HCID 91251276, compound

HRID 1039536Notes

Reaction equation

HRID 1039536 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[C:12]2[O:13][CH:14]=[CH:15][C:11]=2[C:10]([O:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:9][CH:8]=1.O>ClCCl>[OH:6][C:7]1[C:12]2[O:13][CH:14]=[CH:15][C:11]=2[C:10]([O:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 86629327HCID 86629327, compound

Product 1

HCID 91251276HCID 91251276, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of boron tribromide (5.50 g, 22 mmol) in dichloromethane (20 mL) was added dropwise to a solution of the above ester (2.77 g, 11.1 mmol) in dichloromethane (30 mL) at −40° C. and the mixture was stirred for 3 h without cooling while the temperature reached 0° C. Water (3 mL) was added to the mixture the organic layer was evaporated in vacuo. The obtained residue was purified by column chromatography (silica gel Fluka 60, chloroform) affording ethyl (7-hydroxybenzo[b]furan-4-yloxy)acetate.

Workup

  1. temperaturewithout cooling while the temperature
  2. customreached 0° C
  3. customwas evaporated in vacuo
  4. customThe obtained residue was purified by column chromatography (silica gel Fluka 60, chloroform)

Sources & evidence

ORD record
ord-67ae16905932474f9ce07c3e14202867
Source dataset
uspto-grants-2013_10
Patent number
US08551993B2

Reaction notes

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