Carbon tetrabromide → HCID 18988240, compound

HRID 2396130Notes

Reaction equation

HRID 2396130 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[CH2:6][CH:7]([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:8]O.C(Br)(Br)(Br)[Br:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:20][CH2:8][CH:7]([CH2:6][C:5]1[CH:14]=[CH:15][C:16]([O:17][CH3:18])=[C:3]([O:2][CH3:1])[CH:4]=1)[CH2:10][CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 18988286HCID 18988286, compound

Product 1

HCID 18988240HCID 18988240, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Part E. The alcohol compound from Part D above (3.39 g, 13.4 mmol) and carbon tetrabromide (5.78 g, 17.4 mmol) were dissolved in methylene chloride (30 mL). This solution was cooled to 0° C. and treated with a 20 mL methylene chloride solution of triphenylphosphine (4.57 g, 17.4 mmol). The solution was allowed to stir for 14 hours, then evaporated. The residual oil was separated by flash chromatography (1:9 ethyl acetate-hexane) to afford the product, 1-bromo-2-(3,4-dimethoxybenzyl)hexane, as an oil (4.01 g, 12.7 mmol, 95%). 1H NMR (CDCl3): δ 6.81-6.71 (3H, m); 3.88 (3H, s); 3.87 (3H, s); 3.41 (1H, dd, J=9.9, 4,4 Hz); 3.33 (1H, dd, J=9.9, 4.0 Hz); 2.64 (1H, dd, J=13.5, 6.2 Hz); 2.58 (1H, dd, J=13.5, 8.0 Hz); 1.90-1.80 (1H, m); 1.48-1.24 (6H, m); 0.91 (3H, t, J=6.8 Hz). Mass spectrum (NH3 -CI/DDIP): m/z 334 (98%); 332 (100%); 317 (33%); 315 (34%); 252 (3%).

Workup

  1. customevaporated
  2. customThe residual oil was separated by flash chromatography (1:9 ethyl acetate-hexane)

Sources & evidence

ORD record
ord-9c93f5b826f44a6e92d2d055c2f3910b
Source dataset
uspto-grants-1996_02
Patent number
US05491152

Reaction notes

Loading…