Diethyl Ether → HCID 67204228, compound

HRID 1036812Notes

Reaction equation

HRID 1036812 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16]O)=[CH:11][C:10]=1[F:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Br)(Br)(Br)[Br:20].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOCC>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][Br:20])=[CH:11][C:10]=1[F:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 672034892-(4-(Benzyloxy)-3-fluorophenyl)ethanol

Product 1

HCID 67204228HCID 67204228, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-benzyloxy-3-fluoro-phenyl)-ethanol (1.0 g, 4.0 mmol) and CBr4 (1.5 g, 4.5 mmol) in CH2Cl2 (10 mL), was PPh3 (1.2 g, 4.5 mmol) added portionwise at 0° C. The reaction mixture stirred for 2 hours at the same temperature. The reaction was concentrated under vacuum and the residue was stirred in ether (10 mmol). The solid, mainly triphenylphosphine oxide, was filtrated off and the filtrate was concentrated under vacuum. The residue was purified over SiO2 to afford the desired compound (1.15 g, 93.5%) as a white crystal. 1H NMR (400 MHz, DMSO-d6) δ 7.36-7.49 (m, 5H), 7.17-7.23 (m, 2H), 7.03-7.05 (m, 1H), 5.18 (s, 2H), 3.72 (t, 2H), 3.08 (t, 2H). LCMS 273.4 [MH+].

Workup

  1. additionadded portionwise at 0° C
  2. concentrationThe reaction was concentrated under vacuum
  3. filtrationThe solid, mainly triphenylphosphine oxide, was filtrated off
  4. concentrationthe filtrate was concentrated under vacuum
  5. customThe residue was purified over SiO2

Sources & evidence

ORD record
ord-69fcf040dd564316b098d2f5e8cf1134
Source dataset
uspto-grants-2013_10
Patent number
US08546429B2

Reaction notes

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