Benzyl Bromide → HCID 71744043, compound

HRID 520375Notes

Reaction equation

HRID 520375 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[O:9]=[C:10]1[CH2:17][CH:16]2[CH:12]([CH2:13][CH:14]([C:18]([OH:20])=[O:19])[CH2:15]2)[CH2:11]1.CCN(C(C)C)C(C)C>C(#N)C.C(Cl)(Cl)Cl>[O:9]=[C:10]1[CH2:17][CH:16]2[CH:12]([CH2:13][CH:14]([C:18]([O:20][CH2:2][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)=[O:19])[CH2:15]2)[CH2:11]1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 81531DiisopropylethylamineHCID 717439625-Oxooctahydropentalene-2-carboxylic acid

Product 1

HCID 71744043HCID 71744043, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

Neat (bromomethyl)benzene (531 mg) was added to a stirred mixture of 5-oxooctahydropentalene-2-carboxylic acid (435 mg) and DIPEA (0.542 mL) in acetonitrile (2.5 mL) and CHCl3 (2.5 mL) and the mixture was stirred at rt overnight. Reaction mixture was evaporated to dryness and purified by silica gel FCC (0-1% MeOH in DCM) to afford benzyl 5-oxooctahydropentalene-2-carboxylate which was isolated as an endo/exo isomeric mixture.

Workup

  1. customReaction mixture
  2. customwas evaporated to dryness
  3. custompurified by silica gel FCC (0-1% MeOH in DCM)

Sources & evidence

ORD record
ord-9bcae2da8061485a8892ac89dd0bc9e8
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

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