Bromine → HCID 12985440, compound

HRID 1666743Notes

Reaction equation

HRID 1666743 reaction equation
[Br:1]Br.[CH3:3][C:4]1([CH3:18])[CH2:13][CH2:12][C:11]2[C:6](=[C:7]([CH3:17])[C:8]([CH3:16])=[C:9]([OH:15])[C:10]=2[CH3:14])[O:5]1>CCCCCC>[Br:1][CH2:14][C:10]1[C:9]([OH:15])=[C:8]([CH3:16])[C:7]([CH3:17])=[C:6]2[C:11]=1[CH2:12][CH2:13][C:4]([CH3:18])([CH3:3])[O:5]2

Participants

4

Reactant 2

HCID 24408BromineHCID 99479Chromanol

Product 1

HCID 12985440HCID 12985440, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Procedure

A solution of Br2 (0.540 mL, 10.5 mmol) in hexane (70 mL) was quickly added to the round bottom flask equipped with a CaCl2 drying tube and containing a stirred solution of 2,2,5,7,8-pentamethyl-6-chromanol (2.20 g, 10.0 mmol) in hexane (340 mL). After stirring the reaction mixture for 2 h the solvents were evaporated yielding of 5-bromomethyl-2,2,7,8-tetramethyl-chroman-6-ol as a pale yellow solid (3.0 g), which was immediately used in the next step without further purification. 1H-NMR (300 MHz, CDCl3) δ (ppm): 4.68 (s, 2H), 2.81 (t, J=7, 2H), 2.17 (s, 3H), 2.14 (s, 3H), 1.84 (t, J=7, 2H), 1.32 (s, 6H). MS (ESI-Pos) m/z 219.2 (M-Br+).

Workup

  1. customequipped with a CaCl2 drying tube
  2. customwere evaporated

Sources & evidence

ORD record
ord-1b1f4b433b704bc5812c9db420658a7d
Source dataset
uspto-grants-2011_10
Patent number
US08044097B2

Reaction notes

Loading…