2-Bromo-6-methoxynaphthalene → (2-Fluoro-4-methoxyphenyl)(6-methoxy-2-naphthyl)methanol

HRID 1061848Notes

Reaction equation

C([Li])CCC.Br[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH3:18])[CH:13]=2)[CH:8]=1.[F:19][C:20]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:21]=1[CH:22]=[O:23]>C1COCC1>[F:19][C:20]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:21]=1[CH:22]([C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH3:18])[CH:13]=2)[CH:8]=1)[OH:23]

Participants

Conditions

Temperature: -78 °C

Procedure

n-Butyllithium (2.5 M, 16.9 mL) was added dropwise into a cold (−78° C.) solution of 2-bromo-6-methoxynaphthalene (10.0 g, 42.2 mmol), and THF (200 mL). The reaction mixture was stirred at −78° C. for 2 h, and then 2-fluoro-4-methoxybenzaldehyde (6.5 g, 42 2 mmol) in THF (10 mL) was added. The mixture was allowed to warm up to 0° C. stirred for 10 min, and then quenched with aqueous ammonium cholride. The mixture was poured into water, acidified with HCl (2N) and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography (hexanes/EtOAc 3/1) gave a brown solid (12.2 g, 93% yield, m.p. 68-69° C.); MS m/e 312 (M+).

Workup

temperatureto warm up to 0° C.
stirringstirred for 10 min
customquenched with aqueous ammonium cholride
additionThe mixture was poured into water
extractionextracted with EtOAc
dry with materialThe organic extracts were dried over MgSO4
customEvaporation and purification by flash chromatography (hexanes/EtOAc 3/1)

Sources & evidence

ORD record: ord-0176a36bd1764994a0db7dd75f3aa34d
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06960607B2

Reaction notes

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