Boron tribromide → HCID 25149596, compound

HRID 1170967Notes

Reaction equation

[I:1][C:2]1[CH:3]=[C:4]([OH:21])[CH:5]=[C:6]([I:20])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15]C)=[C:11]([CH:17]([CH3:19])[CH3:18])[CH:10]=1.B(Br)(Br)Br>ClCCl>[I:1][C:2]1[CH:3]=[C:4]([OH:21])[CH:5]=[C:6]([I:20])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([CH:17]([CH3:19])[CH3:18])[CH:10]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a stirred solution of 3,5-diiodo-4-(4′-methoxy-3′-iso-propylphenoxy)phenol (0.28 g, 0.55 mmol) in dichloromethane (17.0 mL) at −78° C. was added BBr3 (13.1 mL, 13.1 mmol, 1.0 M solution in CH2Cl2). The reaction mixture was stirred at −78° C. for 10 min, allowed to warm to room temperature and stirred for 16 h. The reaction mixture was poured into ice and extracted with CH2Cl2 (20 mL×2). The organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel, eluting with acetone-hexanes (3:7) to afford 3,5-diiodo-4-(4′-hydroxy-3′-iso-propylphenoxy)phenol as an off-white solid (0.18 g, 66%): 1H NMR (300 M , DMSO-d6): δ 9.95 (s, 1 H), 8.91 (s, 1 H), 7.27 (s, 2 H), 6.62 (d, J=9.0 Hz, 1 H), 6.56 (d, J=3.0 Hz, 1 H), 6.18 (m, 1 H), 3.72 (s, 3 H), 3.14 (m, 1 H), 1.10 (d, J=6.0 Hz, 6 H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=hexanes-acetone (7:3); Rf=0.28.

Workup

temperatureto warm to room temperature
stirringstirred for 16 h
additionThe reaction mixture was poured into ice
extractionextracted with CH2Cl2 (20 mL×2)
dry with materialThe organic layers were dried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude product was purified by column chromatography on silica gel
washeluting with acetone-hexanes (3:7)

Sources & evidence

ORD record: ord-9db4c03fdc19483bbf0bd16879965731
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07829552B2

Reaction notes

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