Calcium Carbonate → 4'-Chloro-5-fluoro-[1,1'-biphenyl]-2-carbaldehyde

HRID 376442Notes

Reaction equation

HRID 376442 reaction equation
BrBr.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[CH3:17])=[CH:6][CH:5]=1.C(=O)([O-])[O-:19].[Ca+2]>O>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[CH:17]=[O:19])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 10112Calcium CarbonateHCID 24408BromineHCID 193619384-Chloro-5'-fluoro-2'-methylbiphenyl

Product 1

HCID 193619434'-Chloro-5-fluoro-[1,1'-biphenyl]-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Bromine (67 g) is added slowly to a stirred solution of 4-chloro-5'-fluoro-2'-methylbiphenyl (of 46.9 g) while being illuminated. The temperature is kept between 105-110° C. for 1 hour. Water (120 ml) and calcium carbonate (90 g) are then added to this product with stirring at reflux for 20 hours. The organics are extracted with chloroform (400 ml.), and the organic phase is washed with water, separated and dried (MgSO4). The chloroform is evaporated. The residue is recrystallized from hexane.

Workup

  1. customwhile being illuminated
  2. temperatureat reflux for 20 hours
  3. extractionThe organics are extracted with chloroform (400 ml.)
  4. washthe organic phase is washed with water
  5. customseparated
  6. dry with materialdried (MgSO4)
  7. customThe chloroform is evaporated
  8. customThe residue is recrystallized from hexane

Sources & evidence

ORD record
ord-6c0661cb23e24e4790217d14ef7d6e09
Source dataset
uspto-grants-2000_02
Patent number
US06020379

Reaction notes

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