N-bromobutanimide → 2-[2-(Bromomethyl)-1-naphthyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 629850Notes

Reaction equation

HRID 629850 reaction equation
[CH3:1][C:2]1([CH3:20])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11][C:10]=2[CH3:19])[O:3]1.C1C(=O)N([Br:28])C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:28][CH2:19][C:10]1[CH:11]=[CH:12][C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]=1[B:4]1[O:3][C:2]([CH3:20])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 222401864,4,5,5-Tetramethyl-2-(2-methylnaphthalen-1-yl)-1,3,2-dioxaborolane

Product 1

HCID 667958652-[2-(Bromomethyl)-1-naphthyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneYield 101.8%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 47.3 g (176 mmol) of 4,4,5,5-tetramethyl-2-(2-methyl-1-naphthyl)-1,3,2-dioxaborolane, 33.0 g (185 mmol) of NBS, and 0.17 g (0.70 mmol) of benzoyl peroxide in 340 ml of CCl4 was stirred in argon atmosphere for 14 h at 75° C. The resulting mixture was cooled to room temperature, filtered through a glass frit (G3), and the filtrate was evaporated to dryness. This procedure gave 62.2 g (99%) of a beige solid. Anal. calc. for C17H20BBrO2: C, 58.83; H, 5.81. Found: C, 58.75; H, 5.90. 1H NMR (CDCl3): δ 8.30 (m, 1H, 8-H), 7.84 (d, J=8.3 Hz, 1H, 4-H), 7.79 (m, 1H, 5-H), 7.43-7.52 (m, 3H, 3,6,7-H), 4.96 (s, 2H, CH2Br), 1.51 (s, 12H, CMe2CMe2).

Workup

  1. temperatureThe resulting mixture was cooled to room temperature
  2. filtrationfiltered through a glass frit (G3)
  3. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-977533999c344a7dbc2f38c39adda3a9
Source dataset
uspto-grants-2016_04
Patent number
US09315526B2

Reaction notes

Loading…