Methanol → HCID 67299283, compound

HRID 1958695Notes

Reaction equation

HRID 1958695 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[S:12][C:11]([C:13]([O:15][CH3:16])=[O:14])=[CH:10][C:9]=1[C:17]1[CH:22]=[CH:21][C:20]([O:23]C)=[CH:19][CH:18]=1.B(Br)(Br)Br.CO>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[S:12][C:11]([C:13]([O:15][CH3:16])=[O:14])=[CH:10][C:9]=1[C:17]1[CH:18]=[CH:19][C:20]([OH:23])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 67299510HCID 67299510, compound

Product 1

HCID 67299283HCID 67299283, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5 g of the compound obtained in stage 23D) are added to 100 ml of CH2Cl2, cooling is carried out at −50° C. and 41.8 ml of 1M solution of BBr3 in CH2Cl2 are added. The temperature is allowed to return to 20° C. and then 20 ml of methanol are added. The mixture is concentrated to dryness and the residue is taken up in CH2Cl2, washed with water, dried over MgSO4 and concentrated to dryness. After purifying by chromatography on silica (heptane up to heptane/AcOEt 75/25), 4.57 g of the expected compound are obtained.

Workup

  1. temperaturecooling
  2. customis carried out at −50° C.
  3. customto return to 20° C.
  4. concentrationThe mixture is concentrated to dryness
  5. washwashed with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to dryness
  8. customAfter purifying by chromatography on silica (heptane up to heptane/AcOEt 75/25), 4.57 g of the expected compound
  9. customare obtained

Sources & evidence

ORD record
ord-22819568d684401a83f3fcb35a66733a
Source dataset
uspto-grants-2013_04
Patent number
US08410137B2

Reaction notes

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