Carbon tetrabromide → HCID 12749167, compound

HRID 493442Notes

Reaction equation

HRID 493442 reaction equation
O[CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[C:5]([C:13]#[N:14])[CH:4]=1.C(Br)(Br)(Br)[Br:16].P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>ClCCCl>[Br:16][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[C:5]([C:13]#[N:14])[CH:4]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 127491664-(Hydroxymethyl)naphthalene-2-carbonitrile

Product 1

HCID 12749167HCID 12749167, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 4-(hydroxymethyl)-2-naphthalenecarbonitrile (200 mg) in dry DCE (5 mL), CBr4 (542.8 mg) and (Ph)3P were added, the resulting mixture was stirred at r.t. for 40 min and then quenched with 40 mL of water. The aqueous phase washed with DCM (3×40 mL). The combined organic extracts were dried, concentrated, and purified by flash chromatography (CH/AcOEt from 8:2 to 1:1) to give the title compound (216 mg) as a white foam.

Workup

  1. customquenched with 40 mL of water
  2. washThe aqueous phase washed with DCM (3×40 mL)
  3. customThe combined organic extracts were dried
  4. concentrationconcentrated
  5. custompurified by flash chromatography (CH/AcOEt from 8:2 to 1:1)

Sources & evidence

ORD record
ord-f25a08a9022240619907e8621b487084
Source dataset
uspto-grants-2009_05
Patent number
US07534893B2

Reaction notes

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