4-Fluorobenzoyl chloride → HCID 59375062, compound

HRID 1811076Notes

Reaction equation

HRID 1811076 reaction equation
[CH3:1][C:2]1[C:8]([B:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]2)=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[F:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1>CCOC(C)=O>[F:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([NH:4][C:3]2[CH:5]=[CH:6][CH:7]=[C:8]([B:9]3[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]3)[C:2]=2[CH3:1])=[O:24])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 467380052-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline2×

Product 1

HCID 59375062HCID 59375062, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (Intermediate 50-1, 1.10 g, 4.72 mmol) in EtOAc (25 mL) was treated with TEA (0.789 mL, 5.66 mmol), then with 4-fluorobenzoyl chloride (0.577 mL, 4.81 mmol) and the mixture was stirred at rt. After 22 h, the mixture was diluted with EtOAc, washed twice with water, then with brine, and dried and concentrated to provide 4-fluoro-N-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzamide as a glassy foam (1.705 g, ca. 90% purity, 92%). 1H NMR (400 MHz, chloroform-d) δ 7.96 (d, J=7.5 Hz, 1H) 7.90 (dd, J=8.6, 5.3 Hz, 2H) 7.66 (dd, J=7.4, 1.2 Hz, 1H) 7.63 (br. s., 1H) 7.22-7.29 (m, 1H) 7.18 (t, J=8.6 Hz, 2H) 2.53 (s, 3H) 1.36 (s, 12H). Mass spectrum m/z 356.1 (M+H)+.

Workup

  1. washwashed twice with water
  2. dry with materialwith brine, and dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4e8cff944bc94bf8919f409c2dce117c
Source dataset
uspto-grants-2013_01
Patent number
US08362065B2

Reaction notes

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