Phosphorus tribromide → HCID 58230567, compound

HRID 390397Notes

Reaction equation

HRID 390397 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21]O)=[C:17]([O:23][CH3:24])[CH:16]=2)=[CH:9][C:8]=1[F:25])[CH3:2].P(Br)(Br)[Br:28]>ClCCl.O>[Br:28][CH2:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][O:13][C:10]2[CH:11]=[CH:12][C:7]([CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:26])=[C:8]([F:25])[CH:9]=2)=[CH:16][C:17]=1[O:23][CH3:24]

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 58230572HCID 58230572, compound

Product 1

HCID 58230567HCID 58230567, compoundYield 93.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-[2-fluoro-4-(4-hydroxymethyl-3-methoxy-benzyloxy)-phenyl]-propionic acid ethyl ester (1.0 g, 2.76 mmol) in dichloromethane (25 mL) is added phosphorus tribromide (0.4 mL, 4.41 mmol) at 0° C. and the reaction mixture is stirred for 15 min at 0° C. The mixture is cooled to 0° C., diluted with water, and extracted with dichloromethane (2×100 mL). The combined extracts are washed with saturated brine, dried over Na2SO4, filtered, and concentrated to give the title compound (1.1 g, crude). 1H NMR (DMSO, 400 MHz) δ 7.34-7.32 (d, J=8 Hz, 1H), 7.12-7.08 (t, J=8 Hz, 1H), 6.96-6.94 (d, J=8 Hz, 2H), 6.67-6.64 (d, J=12 Hz, 2H), 4.98 (s, 2H), 4.55 (s, 2H), 4.12-4.09 (q, 2H), 2.90-2.88 (t, 2H), 2.60-2.56 (t, J=8 Hz, 2H), 1.25-1.22 (t, J=8 Hz, 3H).

Workup

  1. temperatureThe mixture is cooled to 0° C.
  2. extractionextracted with dichloromethane (2×100 mL)
  3. washThe combined extracts are washed with saturated brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4caaec697f8c4d9eabafd64eea9d1624
Source dataset
uspto-grants-2013_02
Patent number
US08383642B2

Reaction notes

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