Hydrogen Bromide → HCID 9969884, compound

HRID 2308022Notes

Reaction equation

HRID 2308022 reaction equation
[C:1]1([C@@H:7]([NH:9][C:10](=[O:23])[CH2:11][C@H:12]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH2:13][CH2:14]O)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Br)(Br)[Br:25].Br>C(OCC)C>[C:1]1([C@@H:7]([NH:9][C:10](=[O:23])[CH2:11][C@H:12]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH2:13][CH2:14][Br:25])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 24614Phosphorus tribromideHCID 9858056HCID 9858056, compound

Product 1

HCID 9969884HCID 9969884, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 4.5 g of alcohol 8 250 mL of dry ethyl ether in an ice bath was added dropwise of 1.7 mL of phosphorous tribromide. After stirring for 3 days in an ice bath, 0.5 mL of conc. hydrobromic acid was added to this mixture. The resulting solution was stirred continuously at room temperature overnight, and 100 mL of ice was added to quench the reaction. The white solid was collected, dissolved in ethyl acetate, washed with saturated sodium hydrocarbonate solution and saturated brine. The organic layer was filtered through a silica gel pad. After the solvent evaporated, the crude solid was recrystallized from ethyl acetate and hexanes to form 3.8 g of the title compound as a white solid (72% yield, >95% de): mp 156.5-157.5 ° C.; [α]25D=−38.2 (c 1.0, CH3OH); 1H NMR (200 MHz, CDCl3) δ 7.40-7.10 (m, 7 H), 6.99 (m, 2 H), 5.52 (br d, J=7.6 Hz, 1 H), 4.98 (m, 1 H), 3.35-3.20 (m, 2 H), 3.05 (m, 1 H), 2.51 (dd, J=6.3, 14.0 Hz, 1 H), 2.37 (dd, J=8.7, 14.0 Hz, 1 H), 2.25-2.05 (m, 2 H), 1.25 (d, J=6.9 Hz, 3 H); 13C NMR (125 MHz, CDCl3) δ 169.7, 161.8, 142.8, 137.7, 129.1, 128.6, 127.4, 126.1, 115.7, 48.6, 44.0, 40.6, 38.7, 30.9, 21.3. Anal. Calcd for C19H21BrFNO: C, 60.33; H, 5.60; N, 3.70. Found: C, 60.57; H, 5.54; N, 3.82.

Workup

  1. stirringThe resulting solution was stirred continuously at room temperature overnight
  2. customto quench
  3. customthe reaction
  4. customThe white solid was collected
  5. dissolutiondissolved in ethyl acetate
  6. washwashed with saturated sodium hydrocarbonate solution and saturated brine
  7. filtrationThe organic layer was filtered through a silica gel pad
  8. customAfter the solvent evaporated
  9. customthe crude solid was recrystallized from ethyl acetate and hexanes

Sources & evidence

ORD record
ord-322a08148f1f4c74a18571ae401d7297
Source dataset
uspto-grants-2004_12
Patent number
US06833458B2

Reaction notes

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