Phosphorus tribromide → HCID 58982104, compound

HRID 1182477Notes

Reaction equation

HRID 1182477 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]O)=[O:12].P(Br)(Br)[Br:22].C(=O)(O)[O-].[Na+]>CCOCC>[Br:22][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:11]([C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)=[O:12]

Participants

5

Reactant 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 23072385HCID 23072385, compound

Product 1

HCID 58982104HCID 58982104, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 7-(2-naphthoyl)-1-heptanol 71 (175 mg, 0.606 mmol) in ether (5 mL) at 0° C. was added a solution of phosphorous tribromide (86 μL, 0.908 mmol) in ether (1 mL) dropwise and the reaction mixture was stirred at room temperature for 6 hours. Saturated sodium bicarbonate solution was added slowly and the mixture was extracted with ether (2×20 mL). The combined organic layers were washed with brine and dried (MgSO4). The solvents were removed in vacuo to give the title compound 72 (141 mg, 70%). 1H NMR (400 MHz, DMSO-d6): δ 8.66 (s, 1H), 8.12 (m, 1H), 7.99 (m, 3H), 7.62 (m, 2H), 3.50 (t, 2H), 3.11 (t, 2H), 1.65 (m, 2H), 1.55 (m, 2H),1.31 (m, 6H).

Workup

  1. extractionthe mixture was extracted with ether (2×20 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-5f87db4314f04675b9ea67a279e5428f
Source dataset
uspto-grants-2007_10
Patent number
US07288567B2

Reaction notes

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