1,3-Dibromopropane → 6-(3-Bromo-propoxy)-4'-trifluoromethyl-biphenyl-3-carboxylic acid methyl ester

HRID 1392282Notes

Reaction equation

HRID 1392282 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[C:8]([OH:11])=[CH:9][CH:10]=1)=[O:4].[Br:22][CH2:23][CH2:24][CH2:25]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:19])([F:20])[F:21])=[CH:14][CH:13]=2)[C:8]([O:11][CH2:25][CH2:24][CH2:23][Br:22])=[CH:9][CH:10]=1)=[O:4]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 69196371Methyl 6-hydroxy-4'-(trifluoromethyl)-[1,1'-biphenyl]-3-carboxylate

Product 1

HCID 691956816-(3-Bromo-propoxy)-4'-trifluoromethyl-biphenyl-3-carboxylic acid methyl esterYield 73%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 6-hydroxy-4′-trifluoromethyl-biphenyl-3-carboxylic acid methyl ester (1.20 g, 4.05 mmol) and 1,3-dibromopropane (4.09 g, 20.3 mmol) in acetone (125 mL) was added potassium carbonate (2.80 g, 20.3 mmol). The reaction mixture was heated to reflux for 3 hours and allowed to cool back down to room temperature. The mixture was partitioned between ethyl acetate and brine, and the layers were separated. The aqueous layer was extracted with one additional portion of ethyl acetate. The organics were combined, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The crude oil was purified by flash chromatography through silica gel using ethyl acetate/hexanes (0/100 gradient to 9/91) to give 6-(3-bromo-propoxy)-4′-trifluoromethyl-biphenyl-3-carboxylic acid methyl ester (1.23 g, 73%) as a white powder. 1H NMR (400 MHz, CDCl3); δ 8.03 (d, 1H), 7.99 (s, 1H), 7.61 (AA′BB′, 4H), 7.02 (d, 1H), 4.18 (t, 2H), 3.88 (s, 3H), 3.43 (t, 2H), 2.23 (m, 2H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3 hours
  3. customThe mixture was partitioned between ethyl acetate and brine
  4. customthe layers were separated
  5. extractionThe aqueous layer was extracted with one additional portion of ethyl acetate
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude oil was purified by flash chromatography through silica gel

Sources & evidence

ORD record
ord-7a92aa2b42be42b78dc848884f158337
Source dataset
uspto-grants-2008_03
Patent number
US07342039B2

Reaction notes

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