Hydrochloric Acid → HCID 67326361, compound

HRID 1257075Notes

Reaction equation

HRID 1257075 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14](C=O)=[C:13]([B:19]2[O:23][C:22](C)(C)C(C)(C)[O:20]2)[CH:12]=1)[C:5]#[N:6].[BH4-].[Na+].Cl>CO>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]2[CH2:22][O:23][B:19]([OH:20])[C:13]=2[CH:12]=1)[C:5]#[N:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 86654959HCID 86654959, compound

Product 1

HCID 67326361HCID 67326361, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-fluoro-4-[4-formyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxy]-benzonitrile (4) (8.23 g, 22.4 mmol) in MeOH (anhydrous, 150 mL) was added NaBH4 (2.56 g, 67.2 mmol) slowly. The reaction was stirred at room temperature for 2 hours, then 1 M HCl (50 mL) was slowly added. The reaction was stirred over night. The methanol was evaporated under vacuum. Much of white solid was formed during the evaporation. The solid was filtered, washed with water, and air-dried to afford 3-fluoro-4-(1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-6-yloxy)-benzonitrile (5) 4.5 g in 75% yield. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.24 (s, 1 H), 8.06 (dd, J=10.94, 1.95 Hz, 1 H), 7.67 (d, J=8.60 Hz, 1 H), 7.49 (d, J=8.21 Hz, 1 H), 7.36 (d, J=2.34 Hz, 1 H), 7.29 (dd, J=8.21, 2.34 Hz, 1 H), 7.13 (t, J=8.40 Hz, 1 H), 4.98 (s, 2 H). ESMS (m/z): 268 (M−H)−. HPLC: 95.27% (220 nm), 97.09% (254 nm), 97.20% (maxplot).

Workup

  1. stirringThe reaction was stirred over night
  2. customThe methanol was evaporated under vacuum
  3. customMuch of white solid was formed during the evaporation
  4. filtrationThe solid was filtered
  5. washwashed with water
  6. customair-dried

Sources & evidence

ORD record
ord-7d20a95b23c84846936420c793e0e9e4
Source dataset
uspto-grants-2013_06
Patent number
US08461336B2

Reaction notes

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