Diboron → HCID 13732856, compound

HRID 1731805Notes

Reaction equation

HRID 1731805 reaction equation
B#B.[F:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=1[C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16](O)=[O:17]>O1CCCC1>[F:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=1[C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[CH2:16][OH:17]

Participants

4

Reactant 2

HCID 6328200DiboronHCID 137328522'-Fluoro-5'-nitro[1,1'-biphenyl]-3-carboxylic acid

Product 1

HCID 13732856HCID 13732856, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1M solution (200 ml) of diborane in tetrahydrofuran was added to a stirred solution of 3-(2-fluoro-5-nitrophenyl)-benzoic acid (6.6 g) in 500 ml tetrahydrofuran. The reaction mixture was stirred at room temperature for 12 hours and then quenched with water and extracted with ethyl acetate. The organic extracts were dried and evaporated to yield a yellow solid which was purified by elution on silica gel with 40% ethyl acetate/hexanes. This gave the pure required product as a yellow solid (4.04 g, 65% yield), m.p. 113°-114° C. NMR (CDCl3, 250 MHz): 8.42 (four line multiplet, 1H), 8.25 (8 line multiplet, 1H), 7.55 (m, 4H), 7.3 (four line multiplet, 1H), 4.8 (d, 2H, J=4.5 Hz), 0.9 (t, 1H).

Workup

  1. customquenched with water
  2. extractionextracted with ethyl acetate
  3. customThe organic extracts were dried
  4. customevaporated
  5. customto yield a yellow solid which
  6. customwas purified by elution on silica gel with 40% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-2b1fb3f715fa4751844389b8f035a804
Source dataset
uspto-grants-1986_11
Patent number
US04623650

Reaction notes

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