Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 118198345, compound

HRID 2177393Notes

Reaction equation

HRID 2177393 reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.C1(P(=[CH:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>>[Br:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1/[CH:4]=[CH:30]/[C:31]([O:33][CH2:34][CH3:35])=[O:32]

Participants

3

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 110848662-Bromo-4-hydroxybenzaldehyde

Product 1

HCID 118198345HCID 118198345, compound

Conditions

Temperature
90 °C

Procedure

Into a 250-mL round-bottom flask, was placed 2-bromo-4-hydroxybenzaldehyde (2.0 g, 9.95 mmol, 1.00 equiv), ethyl (triphenylphosphoranylidene)acetate (5.22 g, 14.98 mmol, 1.51 equiv), Tol (50 mL). The resulting solution was stirred overnight at 90° C. in an oil bath. The reaction progress was monitored by TLC (ethyl acetate/petroleum ether=1:2). The resulting mixture was concentrated under reduced pressure. The residue was purified on a silica gel column, eluting with ethyl acetate/petroleum ether (1:4). This resulted in 2.2 g (77%) of ethyl (2E)-3-(2-bromo-4-hydroxyphenyl)prop-2-enoate as a white solid.

Workup

  1. customInto a 250-mL round-bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under reduced pressure
  3. customThe residue was purified on a silica gel column
  4. washeluting with ethyl acetate/petroleum ether (1:4)
  5. customThis resulted in 2.2 g (77%) of ethyl (2E)-3-(2-bromo-4-hydroxyphenyl)prop-2-enoate as a white solid

Sources & evidence

ORD record
ord-ded199d449ae4a7380cd0ac607aeb260
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

Loading…