1-Bromo-3-chloropropane → Methyl 4'-(3-chloropropoxy)[1,1'-biphenyl]-4-carboxylate

HRID 429235Notes

Reaction equation

HRID 429235 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:25][CH2:26][CH2:27][Cl:28]>CC(=O)CC.C(OCC)(=O)C>[Cl:28][CH2:27][CH2:26][CH2:25][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 1490289Methyl 4'-hydroxy(1,1'-biphenyl)-4-carboxylate

Product 1

HCID 18354767Methyl 4'-(3-chloropropoxy)[1,1'-biphenyl]-4-carboxylateYield 92%

Reagents, catalysts & solvents 2

HCID 6569Methyl Ethyl KetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product from Example 10A (4.50 g, 19.7 mmol), K2CO3 (4.0 g, 29.6 mmol) and 3-bromochloropropane (3.88 g, 24.6 mmol) in 2-butanone (100 mL) were heated at reflux for 24 hours. The mixture was allowed to cool to ambient temperature and then diluted with ethyl acetate (200 mL). The mixture was washed with water (2×100 mL) and brine (100 mL) and the remaining organic layer was dried over MgSO4 and filtered. The filtrate was evaporated under reduced pressure to provide the title compound as an off-white solid (5.5 g, 92% yield).

Workup

  1. temperatureat reflux for 24 hours
  2. washThe mixture was washed with water (2×100 mL) and brine (100 mL)
  3. dry with materialthe remaining organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-0b58d5c83d9549f7872273283ba15296
Source dataset
uspto-grants-2001_11
Patent number
US06316475B1

Reaction notes

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