Phenol → HCID 59816114, compound

HRID 1176828Notes

Reaction equation

HRID 1176828 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5]C=CC=1.C(Br)[C:9]1[CH:14]=CC=CC=1.[H-].[Na+].C[O:19][CH2:20][O:21][C:22]1[CH:31]=[CH:30][C:29]2[O:28][CH:27]([C:32]3[CH:37]=[CH:36][C:35](OCOC)=[CH:34][CH:33]=3)C3CC(O)CC3[C:24]=2[CH:23]=1.CN(C=[O:50])C>>[CH2:14]([O:50][C:1]([C:6]1[C:20](=[O:19])[O:21][C:22]2[C:23]([CH:5]=1)=[CH:24][C:29]([O:28][CH2:27][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)=[CH:30][CH:31]=2)=[O:7])[CH3:9]

Participants

6

Reactant 5

HCID 996PhenolHCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 68706007HCID 68706007, compound

Product 1

HCID 59816114HCID 59816114, compound

Procedure

To a 0 C solution of the phenol (26.7 g, 114 mmol) and benzyl bromide (20.5 mL, 171 mmol) in DMF (300 mL) add NaH (6.84 g, 1.5 mmol) portionwise over 15 min. Allow venting during the addition, during which time the solution turns dark red. After 30 min, remove the cooling bath and allow the solution to warm to 23 C, during which time a precipitate forms and the solution turns dark brown. After 2 h, slowly pour the solution into ½ satd. NaHCO3 (500 mL), and filter the mixture. Wash the filter cake with H2O (2×300 mL) and 50% Et2O/hexanes (2×300 mL.) to remove remaining aqueous salts and excess benzyl bromide. Dry the remaining yellow solid to afford Preparation 27 (28.9 g, 78%). 1H NMR (d-DMSO) δ 8.67 (s, 1 H), 7.57 (s, 1 H), 7.37-7.47 (m, 7 H), 5.15 (s, 2 H), 4.28 (q, J=7.2 Hz, 2 H), 1.31 (t, J=7.2 Hz, 3 H).

Workup

  1. additionAllow venting during the addition, during which time the solution
  2. customremove the cooling bath
  3. temperatureto warm to 23 C, during which time a precipitate forms
  4. waitAfter 2 h
  5. additionslowly pour the solution into ½ satd
  6. filtrationNaHCO3 (500 mL), and filter the mixture
  7. washWash the filter cake with H2O (2×300 mL) and 50% Et2O/hexanes (2×300 mL.)
  8. customto remove
  9. customDry the remaining yellow solid
  10. customto afford

Sources & evidence

ORD record
ord-e54ddbbd627f41f48ed1a8be7c0cc7c2
Source dataset
uspto-grants-2010_11
Patent number
US07842822B2

Reaction notes

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