Phenol → HCID 89582694, compound

HRID 1501060Notes

Reaction equation

HRID 1501060 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([OH:11])[CH2:6][CH2:5]2.[C:12]1(O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6][CH2:5]2

Participants

6

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 134862995-bromo-2,3-dihydro-1H-inden-1-ol

Product 1

HCID 89582694HCID 89582694, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-bromo-2,3-dihydro-1H-inden-1-ol (1 g, 4.7 mmol), phenol (835 mg, 8.9 mmol) and triphenylphosphine (1.8 g, 6.9 mmol) in anhydrous tetrahydrofuran (70 mL) was stirred at 0° C. under nitrogen atmosphere. To this mixture was added dropwise diisopropyl azodicarboxylate (1.4 g, 6.9 mmol) over 5 minutes. Until TLC indicated that starting material was consumed, the solvent was evaporated in vacuo and the resulting oil was purified by column chromatography (silica gel, hexane/ethyl acetate=1/1) to give the product 5-bromo-1-phenoxy-2,3-dihydro-1H-indene (1.1 g, 85%) as a white solid. LRMS (M+H+) m/z: calcd 288.01. found 288. 1H NMR (300 MHz, CDCl3): δ 7.46-7.27 (m, 6H), 7.02 (s, 1H), 6.99-6.98 (m, 1H), 5.73-5.70 (m, 1H), 3.14-3.09 (m, 1H), 2.96-2.95 (m, 1H), 2.59-2.54 (m, 1H), 2.27-2.23 (m, 1H).

Workup

  1. customwas consumed
  2. customthe solvent was evaporated in vacuo
  3. customthe resulting oil was purified by column chromatography (silica gel, hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-8b536e914bce4ec198e9927adf59da2b
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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