Benzyl Bromide → HCID 131733002, compound

HRID 2177394Notes

Reaction equation

HRID 2177394 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1/[CH:9]=[CH:10]/[C:11]([O:13][CH2:14][CH3:15])=[O:12].C(=O)([O-])[O-].[K+].[K+].[CH:22]1[CH:27]=[CH:26][C:25]([CH2:28]Br)=[CH:24][CH:23]=1>CC#N>[CH2:28]([O:8][C:6]1[CH:5]=[CH:4][C:3](/[CH:9]=[CH:10]/[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:2]([Br:1])[CH:7]=1)[C:25]1[CH:26]=[CH:27][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 118198345HCID 118198345, compound

Product 1

HCID 131733002HCID 131733002, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Into a 100-mL round-bottom flask, was placed ethyl (2E)-3-(2-bromo-4-hydroxyphenyl)prop-2-enoate (1.0 g, 3.69 mmol, 1.00 equiv), CH3CN (20 mL), potassium carbonate (1.027 g, 7.43 mmol, 2.01 equiv). This was followed by the addition of BnBr (660 mg, 3.86 mmol, 1.05 equiv) dropwise with stirring. The resulting solution was stirred overnight at 15° C. The reaction progress was monitored by TLC (ethyl acetate/petroleum ether=1:2). The solids were removed by filtration. The resulting mixture was concentrated under reduced pressure. The residue was applied to a silica gel column, eluting with ethyl acetate/petroleum ether (20:80). This resulted in 1.32 g (94%) of ethyl (2E)-3-[4-(benzyloxy)-2-bromophenyl]prop-2-enoate as a light yellow solid.

Workup

  1. customInto a 100-mL round-bottom flask, was placed
  2. stirringThe resulting solution was stirred overnight at 15° C
  3. customThe solids were removed by filtration
  4. concentrationThe resulting mixture was concentrated under reduced pressure
  5. washeluting with ethyl acetate/petroleum ether (20:80)
  6. customThis resulted in 1.32 g (94%) of ethyl (2E)-3-[4-(benzyloxy)-2-bromophenyl]prop-2-enoate as a light yellow solid

Sources & evidence

ORD record
ord-d1639d314f7144849184e44ad6ff1862
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

Loading…