Carbon tetrabromide → HCID 22640082, compound

HRID 2415048Notes

Reaction equation

HRID 2415048 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]1([CH2:26][CH2:27][CH2:28][CH:29]([CH2:39]O)[CH2:30][CH2:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(Br)(Br)(Br)[Br:42]>C(Cl)Cl>[Br:42][CH2:39][CH:29]([CH2:30][CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:28][CH2:27][CH2:26][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 22640067HCID 22640067, compound

Product 1

HCID 22640082HCID 22640082, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of triphenylphosphine (0.885 g, 3.37 mmol) in methylene chloride (5 mL) was added to a solution of yield 1,7-diphenyl-4-hydroxymethylheptane (0.666 g, 2.36 mmol) and carbon tetrabromide (1.10 g, 3.33 mmol) in methylene chloride (10 mL) at 0° C. under nitrogen. After 16 h, the solvent was removed under reduced pressure and the residue was purified by silica gel chromatography, eluting with methylene chloride/hexanes (5% to 10%) to provide 4-bromomethyl-1,7-diphenylheptane (0.723 g, o9%). 1H NMR (300 MHz, CDCl3): δ 1.45 (m, 4 H), 1.63 (m, 5 H), 2.62 (t, 4 H, J=7.6), 3.46 (d, 2 H, J=4.7), 7.25 (m, 10 H).

Workup

  1. customthe solvent was removed under reduced pressure
  2. customthe residue was purified by silica gel chromatography
  3. washeluting with methylene chloride/hexanes (5% to 10%)

Sources & evidence

ORD record
ord-b33f52ba2f7d46f0b000cba63c5c36b6
Source dataset
uspto-grants-2004_11
Patent number
US06818643B1

Reaction notes

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