1,2-Dichloroethane → (2,4-Bis-benzyloxy-5-isopropenyl-phenyl)-(5-bromo-1,3-dihydro-isoindol-2-yl)-methanone

HRID 2355737Notes

Reaction equation

HRID 2355737 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:14][C:10]=1[C:11]([OH:13])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:21][C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[CH2:27][NH:26][CH2:25]2.C(Cl)CCl.[CH:35]1[CH:36]=[CH:37][C:38]2N(O)N=N[C:39]=2[CH:40]=1.CN([CH:48]=[O:49])C>>[CH2:1]([O:8][C:9]1[CH:17]=[C:16]([O:49][CH2:48][C:39]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:40]=2)[C:15]([C:18]([CH3:20])=[CH2:19])=[CH:14][C:10]=1[C:11]([N:26]1[CH2:25][C:24]2[C:28](=[CH:29][CH:30]=[C:22]([Br:21])[CH:23]=2)[CH2:27]1)=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 147958715-BromoisoindolineHCID 666722601285515-85-6

Product 1

HCID 46915776(2,4-Bis-benzyloxy-5-isopropenyl-phenyl)-(5-bromo-1,3-dihydro-isoindol-2-yl)-methanone

Procedure

A solution of benzyloxy-5-isopropyl-benzoic acid (2.85 g; 7.6 mmol), 5-bromo-2,3-dihydro-1H-isoindole (1.5 g; 1 equiv.), EDC (1.175 g; 1.2 equiv.) and HOBt (1.25 g; 1.2 equiv.) in DMF (25 ml) was stirred at room temperature overnight then evaporated. The residue was dissolved in EtOAc, washed with 2M HCl then saturated NaHCO3, dried (MgSO4) and evaporated. Purification using a Biotage SP4 (40S, 40 ml/min) eluting with 1:4-1:3-1:2 EtOAc/P.E. gave 2.45 g of (2,4-bis-benzyloxy-5-isopropenyl-phenyl)-(5-bromo-1,3-dihydro-isoindol-2-yl)-methanone as a light brown solid.

Workup

  1. customthen evaporated
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with 2M HCl
  4. dry with materialsaturated NaHCO3, dried (MgSO4)
  5. customevaporated
  6. customPurification
  7. washeluting with 1:4-1:3-1:2 EtOAc/P.E

Sources & evidence

ORD record
ord-2bf1b95b57334109bf2d3512d9d0d977
Source dataset
uspto-grants-2010_07
Patent number
US07754725B2

Reaction notes

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