3-Bromophenol → HCID 7663500, compound

HRID 658820Notes

Reaction equation

HRID 658820 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.O[CH2:10][CH2:11][N:12]1[C:16](=[O:17])[C:15]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]2[C:13]1=[O:22].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH2:10][CH2:11][N:12]1[C:16](=[O:17])[C:15]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]2[C:13]1=[O:22]

Participants

6

Reactant 4

HCID 115633-BromophenolHCID 11776TriphenylphosphineHCID 77499N-(2-Hydroxyethyl)phthalimideHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 7663500HCID 7663500, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice cold solution of 3-bromophenol (14) (2.0 g, 11.56 mmol), N-(2-hydroxyethyl)phthalimide (2.21 g, 11.6 mmol) and triphenyl phosphine (3.03 g, 11.6 mmol) in anhydrous THF (25 mL) was added diethyl azodicarboxylate (2.57 g, 12.7 mmol) slowly. The reaction mixture was allowed to warm to room temperature and stirred overnight. After concentration under reduced pressure, 50% EtOAc-hexanes (100 mL) was added and the mixture was warmed to 60° C. After cooling to room temperature, the solids were removed by filtration and the filtrate was concentrated under reduced pressure. Purification by flash chromatography (10% EtOAc-hexanes) gave bromide 17 as a white solid. Yield (1.92 g, 48%): 1H NMR (400 MHz, DMSO-d6) δ 7.82-7.88 (m, 4H), 7.19 (t, J=8.4 Hz, 1H), 7.06-7.09 (m, 2H), 6.87-6.90 (m, 1H), 4.22 (t, J=5.6 Hz, 2H), 3.93 (t, J=5.6 Hz, 2H).

Workup

  1. concentrationAfter concentration under reduced pressure, 50% EtOAc-hexanes (100 mL)
  2. additionwas added
  3. temperaturethe mixture was warmed to 60° C
  4. temperatureAfter cooling to room temperature
  5. customthe solids were removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customPurification by flash chromatography (10% EtOAc-hexanes)

Sources & evidence

ORD record
ord-63114d7354964f6299626ad4d6bb81d0
Source dataset
uspto-grants-2011_12
Patent number
US08076516B2

Reaction notes

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