Ethyl orthoformate → 4-Bromo-1-(diethoxymethyl)-2-fluorobenzene

HRID 2060641Notes

Reaction equation

HRID 2060641 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5](C=O)=[C:4]([F:10])[CH:3]=1.C(O[CH:14]([O:18][CH2:19][CH3:20])[O:15][CH2:16][CH3:17])C.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:14]([O:15][CH2:16][CH3:17])[O:18][CH2:19][CH3:20])=[C:4]([F:10])[CH:3]=1

Participants

4

Reactant 3

HCID 31214Ethyl orthoformateHCID 1435174-Bromo-2-fluorobenzaldehydeHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 583352614-Bromo-1-(diethoxymethyl)-2-fluorobenzene

Procedure

The title compound was prepared as described in Example 15, Step 2 using 4-bromo-2-fluorobenzaldehyde (102 g, 0.5 mol), triethylorthoformate (88.8 g, 0.6 mol), and PPTS (2.52 g, 0.05 mol) as starting materials. 1H NMR (400 MHz, CDCl3): δ 7.41 (d, 1H), 7.21 (d, 1H), 7.14 (d, 1H), 5.60 (s, 1H), 3.68 (q, 2H), 3.49 (q, 2H), 1.17 (t, 6H).

Sources & evidence

ORD record
ord-52202d2d49f7475ab24a8df44620e158
Source dataset
uspto-grants-2012_10
Patent number
US08278335B2

Reaction notes

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