4-Fluorophenylboronic acid → HCID 14839518, compound

HRID 1742879Notes

Reaction equation

HRID 1742879 reaction equation
Br[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=2)[CH:3]=1.[F:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1>C(=O)([O-])[O-].[Na+].[Na+]>[CH3:22][O:21][C:15]1[CH:14]=[C:13]([C:4]2[CH:3]=[C:2]([C:27]3[CH:28]=[CH:29][C:24]([F:23])=[CH:25][CH:26]=3)[CH:12]=[CH:11][C:5]=2[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:18]=[CH:17][C:16]=1[O:19][CH3:20]

Participants

4

Reactant 2

HCID 2856454-Fluorophenylboronic acidHCID 14839521HCID 14839521, compound2×

Product 1

HCID 14839518HCID 14839518, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Procedure

1,2-Dimethoxyethane (30 ml) which has been degassed with argon is introduced into a 250 ml three-necked flask, then ethyl 4-bromo-2-(3,4-dimethoxyphenyl)benzoate (3.65 g; 0.010 mole; compound 209), palladium tetrakis(triphenyl)phosphine (0.1 g), 4-fluorophenylboronic acid (1.7 g; 0.012 mole) and 2M sodium carbonate (20 ml) are added. After refluxing for 8 hours, the reaction mixture is poured into distilled water (100 ml). The mixture is then extracted with dichloromethane (2×100 ml), washed with water (100 ml), dried over magnesium sulphate, passed over a layer of silica and then evaporated. Ethyl 2-(3,4-dimethoxyphenyl)-4-(4-fluorophenyl)benzoate (3.4 g; yield: 89.5%) is thus obtained, m.p. 127° C. (compound 233).

Workup

  1. custom1,2-Dimethoxyethane (30 ml) which has been degassed with argon
  2. additionis introduced into a 250 ml three-necked flask
  3. temperatureAfter refluxing for 8 hours
  4. additionthe reaction mixture is poured
  5. distillationinto distilled water (100 ml)
  6. extractionThe mixture is then extracted with dichloromethane (2×100 ml)
  7. washwashed with water (100 ml)
  8. dry with materialdried over magnesium sulphate
  9. customevaporated

Sources & evidence

ORD record
ord-d3ac191c37e64cd887410f17097f395b
Source dataset
uspto-grants-1994_08
Patent number
US05342835

Reaction notes

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