Benzyl Bromide → HCID 5314864, compound

HRID 1005424Notes

Reaction equation

HRID 1005424 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][C:12]([OH:14])=[O:13].C1CCN2C(=NCCC2)CC1.[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(#N)C>[CH2:26]([O:13][C:12](=[O:14])[CH2:11][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 113932-Naphthaleneacetic acidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 5314864HCID 5314864, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 2-naphthylacetic acid (1 g, 5.4 mmol) in acetonitrile (10 mL) were added DBU (0.97 mL, 6.4 mmol) and benzyl bromide (0.77 mL, 6.4 mmol). After 3 hours the mixture was concentrated, and the residue was taken up in ethyl acetate. The organic phase was washed with 10% citric acid, 10% NaHCO3 and brine, dried (MgSO4), and concentrated to give 2-naphthylacetic acid benzyl ester as a white solid (1.5 g, 100%).

Workup

  1. concentrationAfter 3 hours the mixture was concentrated
  2. washThe organic phase was washed with 10% citric acid, 10% NaHCO3 and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e9e2e8b4b741438f9746e7d8ccc52a1a
Source dataset
uspto-grants-2000_04
Patent number
US06054470

Reaction notes

Loading…