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

HRID 1076062Notes

Reaction equation

HRID 1076062 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

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

Workup

  1. temperatureat reflux for 20 hours
  2. extractionThe organics are extracted with chloroform (400 ml.)
  3. washthe chloroform washed with water
  4. customseparated
  5. dry with materialdried (MgSO4)
  6. customThe chloroform solution is evaporated to a solid which
  7. customis recrystallized from hexane

Sources & evidence

ORD record
ord-9cc1b17eaa5b4e52baad46b9133e42e6
Source dataset
uspto-grants-1976_05
Patent number
US03954852

Reaction notes

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