Methanol → HCID 67299495, compound

HRID 1958686Notes

Reaction equation

HRID 1958686 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[S:13][C:12]([C:14]([O:16][CH3:17])=[O:15])=[CH:11][C:10]=1[C:18]1[CH:23]=[CH:22][C:21]([O:24]C)=[CH:20][CH:19]=1.B(Br)(Br)Br.CO>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[S:13][C:12]([C:14]([O:16][CH3:17])=[O:15])=[CH:11][C:10]=1[C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 67299339HCID 67299339, compound

Product 1

HCID 67299495HCID 67299495, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The compound obtained in stage 16D) is added to 100 ml of CH2Cl2, cooling is carried out to −50° C. and 40 ml of a 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, MgSO4 and concentrated to dryness. After purifying by chromatography on silica (heptane up to heptane/AcOEt 75/25), 4.8 g of the expected compound are obtained.

Workup

  1. temperaturecooling
  2. customis carried out to −50° C.
  3. customto return to 20° C.
  4. concentrationThe mixture is concentrated to dryness
  5. washwashed with water, MgSO4
  6. concentrationconcentrated to dryness
  7. customAfter purifying by chromatography on silica (heptane up to heptane/AcOEt 75/25), 4.8 g of the expected compound
  8. customare obtained

Sources & evidence

ORD record
ord-098db64f63eb4f5981b2faaf91265081
Source dataset
uspto-grants-2013_04
Patent number
US08410137B2

Reaction notes

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