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

HRID 424100Notes

Reaction equation

HRID 424100 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:15]([C:18]([CH3:20])=[CH2:19])=[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 66672430Benzyloxy-5-isopropenyl-benzoic acid

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-isopropenyl-benzoic acid (2.85 g; 7.6 mmol), 5-bromo-2,3-dihydro-1H-isoindole (1.5 g; 1 equiv.), EDC (1.75 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-6fe71416c0674002b5a775f44c383df5
Source dataset
uspto-grants-2012_01
Patent number
US08101648B2

Reaction notes

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