Carbon tetrabromide → HCID 18005873, compound

HRID 989280Notes

Reaction equation

HRID 989280 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([CH2:12]O)[O:9]2)=[CH:4][CH:3]=1.C(Br)(Br)(Br)[Br:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:15][CH2:12][CH:8]1[CH2:7][CH2:6][C:5]2[C:10](=[CH:11][C:2]([OH:1])=[CH:3][CH:4]=2)[O:9]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 18005881HCID 18005881, compound

Product 1

HCID 18005873HCID 18005873, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of (7-hydroxychroman-2-yl)methanol (6.18 g, 34.3 mmol) and CBr4 (19.3 g, 58.3 mmol) in CH2Cl2 is treated with a solution of triphenylphosphine (9.0 g, 34.3 mmol) in CH2Cl2 at 0° C., stirred at 0° C. for 6 hr and concentrated in vacuo to give a residue. The residue is purified by column chromatography (silica gel, 60% CH2Cl2 in hexanes as eluent) to give the title product as an oil, 4.61 g (55% yield), identified by NMR and mass spectral analyses.

Workup

  1. concentrationconcentrated in vacuo
  2. customto give a residue
  3. customThe residue is purified by column chromatography (silica gel, 60% CH2Cl2 in hexanes as eluent)

Sources & evidence

ORD record
ord-0f5461f37bf74bf5bd6d98b029019835
Source dataset
uspto-grants-2003_10
Patent number
US06638972B2

Reaction notes

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