Hydrochloric Acid → Methyl 2-(benzyloxy)-4-iodobenzoate

HRID 1171438Notes

Reaction equation

HRID 1171438 reaction equation
[I:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17]C=2)[CH:3]=1.C(Br)C1C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].IC1C=CC(C(OC)=O)=C(O)C=1.Cl>CN(C=O)C>[CH2:13]([O:12][C:4]1[CH:3]=[C:2]([I:1])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])[C:14]1[CH:15]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 11380407Methyl 4-iodosalicylateHCID 68769857HCID 68769857, compound

Product 1

HCID 66990993Methyl 2-(benzyloxy)-4-iodobenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The procedure is the same as that followed for methyl 4-iodo-2-phenethyloxybenzoate, using 5.6 ml of benzyl bromide, 14 g of caesium carbonate and 10 g of methyl 4-iodo-2-hydroxybenzoate in 200 ml of DMF. The suspension is stirred for 48 hours at room temperature. The organic phase is acidified at room temperature with a 2N hydrochloric acid solution to pH 5. The desired product is extracted by addition of ethyl ether. The organic phase is washed with water, dried with magnesium sulfate and concentrated using a rotary evaporator. 14 g of the expected compound are recovered in the form of a brown solid.

Workup

  1. extractionThe desired product is extracted by addition of ethyl ether
  2. washThe organic phase is washed with water
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated
  5. customa rotary evaporator
  6. custom14 g of the expected compound are recovered in the form of a brown solid

Sources & evidence

ORD record
ord-bb599a04f2774e2e85d630370d1f6a5d
Source dataset
uspto-grants-2010_11
Patent number
US07829588B2

Reaction notes

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