3-Fluorosalicylaldehyde → HCID 90310583, compound

HRID 1519172Notes

Reaction equation

HRID 1519172 reaction equation
[Li][CH2:2]CCC.[F:6][C:7]1[C:8]([OH:15])=[C:9]([CH:12]=[CH:13][CH:14]=1)[CH:10]=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[F:6][C:7]1[CH:14]=[CH:13][CH:12]=[C:9]([CH:10]=[CH2:2])[C:8]=1[OH:15]

Participants

5

Reactant 2

HCID 5877883-FluorosalicylaldehydeHCID 178418339Butyllithium

Product 1

HCID 90310583HCID 90310583, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a round-bottomed flask containing a stir-bar were added, methyltriphenylphosphonium bromide (5.6 g, 16 mmol) and anhydrous THF (50 mL). The mixture was stirred until homogeneous and then cooled to 0° Celsius. The flask was then charged drop-wise with n-BuLi (6.85 mL, 2.5 M in hexanes). The resultant solution was stirred for 30 minutes and then transferred via cannula to a stirred mixture of 3-fluoro-2-hydroxybenzaldehyde (1 g, 7 mmol) and THF (28 mL) at rt under an argon atmosphere. The resultant mixture was stirred for 3 h before quenching with saturated NH4Cl (50 mL), diluting with water, and extracting with ether (3×100 mL). The combined ethereal extracts were dried over magnesium sulfate, filtered through a plug of silica gel, and then concentrated to dryness to provide the title compound that was used without further purification. 1H NMR (500 MHz, CDCl3) δ 7.20 (m, 1H), 7.04-6.92 (m, 2H), 6.80 (m, 1H), 5.81 (dd, J=17.8, 1.3, 1H), 5.69 (s, 1H), 5.35 (dd, J=11.2, 1.3, 1H).

Workup

  1. additionTo a round-bottomed flask containing a stir-bar
  2. additionwere added
  3. custombefore quenching with saturated NH4Cl (50 mL)
  4. additiondiluting with water
  5. extractionextracting with ether (3×100 mL)
  6. dry with materialThe combined ethereal extracts were dried over magnesium sulfate
  7. filtrationfiltered through a plug of silica gel
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-c231e79dfc5249388bd171733ec98895
Source dataset
uspto-grants-2015_07
Patent number
US09073876B2

Reaction notes

Loading…