Hydrochloric Acid → HCID 17980965, compound

HRID 2219998Notes

Reaction equation

HRID 2219998 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11]3[C:15]([F:17])([F:16])[C:14]([F:19])([F:18])[C:13]([F:21])([F:20])[C:12]=3[C:22]3[C:23]4[CH:31]=[CH:30][C:29]([O:32]C)=[CH:28][C:24]=4[S:25][C:26]=3[CH3:27])=[C:9]([CH3:34])[S:8][C:7]=2[CH:35]=1.B(Br)(Br)Br.Cl>C(Cl)Cl>[OH:32][C:29]1[CH:30]=[CH:31][C:23]2[C:22]([C:12]3[C:13]([F:20])([F:21])[C:14]([F:18])([F:19])[C:15]([F:17])([F:16])[C:11]=3[C:10]3[C:6]4[CH:5]=[CH:4][C:3]([OH:2])=[CH:35][C:7]=4[S:8][C:9]=3[CH3:34])=[C:26]([CH3:27])[S:25][C:24]=2[CH:28]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 17980973HCID 17980973, compound

Product 1

HCID 17980965HCID 17980965, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.60 g (0.01 mol) of the compound obtained in step 3 and 100 mL of pre-distilled CH2Cl2 are introduced into a 3-necked round-bottomed flask under nitrogen. The resulting mixture is cooled by using a ice-water bath, then 4.91 mL (0.05 mol) of BBr3 is added dropwise. The solution is warmed to room temperature and stirred for 6 hours. Then, the mixture is cooled by using a ice-water bath and 100 mL of 10% HCl aqueous solution is added slowly. The chlorinated phase is separated from the aqueous phase. This latter is extracted several times with ethyl acetate. The combined organic phases are washed with water, dried over magnesium sulfate and then are concentrated under reduced pressure. The crude product is purified by column chromatography on silica gel and eluted with mixtures consisting of CH2Cl2 and Et2O of increasing polarity (100:0 to 90:10) to give a white solid (4.7 g, 93% yield).

Workup

  1. temperatureThe resulting mixture is cooled
  2. temperatureThen, the mixture is cooled
  3. customThe chlorinated phase is separated from the aqueous phase
  4. extractionThis latter is extracted several times with ethyl acetate
  5. washThe combined organic phases are washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationare concentrated under reduced pressure
  8. customThe crude product is purified by column chromatography on silica gel
  9. washeluted with mixtures
  10. temperatureof increasing polarity (100:0 to 90:10)

Sources & evidence

ORD record
ord-2306296f0388447fb21fab4ec61fd562
Source dataset
uspto-grants-2008_08
Patent number
US07416682B2

Reaction notes

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