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

HRID 41441Notes

Reaction equation

HRID 41441 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 (40 S, 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-3c191a5763534d15b809c404bf084a2e
Source dataset
uspto-grants-2013_09
Patent number
US08530469B2

Reaction notes

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