Hydrochloric Acid → HCID 59621120, compound

HRID 2061326Notes

Reaction equation

HRID 2061326 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16]C)=[CH:12][CH:11]=2)[CH:3]=1.B(Br)(Br)Br.C(=O)([O-])[O-].[K+].[K+].Cl>ClCCl>[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([CH:3]=1)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 25134Boron tribromideHCID 59621121HCID 59621121, compound

Product 1

HCID 59621120HCID 59621120, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cold solution of 4-iodo-2-(4-methoxy-benzyl)-1-methyl-benzene (12.5 g) in dichloromethane (70 mL) is added a solution of boron tribromide in dichloromethane (1 mol/L, 40 mL). The resulting solution is stirred in the ice-bath for 1 h and at ambient temperature overnight. The solution is then cooled in an ice bath and saturated aqueous potassium carbonate solution is added dropwise. At ambient temperature the mixture is adjusted with aqueous hydrochloric acid (1 mol/L) to a pH of 1, the organic phase is separated, and the aqueous phase is extracted with dichloromethane. The combined organic phases are dried (sodium sulphate) and concentrated in vacuo to give the crude product.

Workup

  1. temperatureThe solution is then cooled in an ice bath
  2. customAt ambient temperature
  3. customthe organic phase is separated
  4. extractionthe aqueous phase is extracted with dichloromethane
  5. dry with materialThe combined organic phases are dried (sodium sulphate)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-249a2561a4c745b196a121469b25b193
Source dataset
uspto-grants-2012_10
Patent number
US08283326B2

Reaction notes

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